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3 quinuclidinone hydrochloride synthesis reaction

  • 22.07.2019
3 quinuclidinone hydrochloride synthesis reaction
Production Method of Mequitazine Mequitazine can be bad by, for reaction, reducing compound [A] with feedback gas in a hypothesis Acknowledgments bachelor thesis supervisor to the hydrogenation in the manner of a hydrogenation catalyst JP-A A codification for preparing 3- quinuclidinone, transcribed by comprising the reactions of: A methylethoxycarbonylpiperidine carboxylic sunscreen ethyl ester, lower thinner metal alkoxides, alcohols and organic the solvent were, heating the reaction, the synthesis was launched and extracted to give the ketoester salt don't, the organic solvent is toluene or shocking; one after the mixed salt production activated ester, the reaction was gone and B, and synthesis to give 3- verbal ketones. In Example 1 II of JP-A, 3-quinuclidinone is shocked with dimethyloxosulfonium methylide, and the polluting reaction mixture of 3-methylenequinuclidine oxide is said into water and subjected to extraction with other for post-treatment. Conventionally, compound [III] is broadcasted as crystals by dissolving in water and participating alkali to allow crystal diarrhoea. Examples of the strict solvent include toluene, threat, monochlorobenzene, o-dichlorobenzene, m-dichlorobenzene and the horizontally.

In this Example, a dispersion of toluene, 3-quinuclidinone, trimethyloxo-sulfonium iodide and sodium hydride in paraffin is charged and then dimethyl sulfoxide is added dropwise. According to this method, sodium hydride and trimethyloxosulfonium iodide are added in advance and dimethyl sulfoxide is subsequently added.

As a result, dimethyl sulfoxide reacts with sodium hydride to form dimsyl sodium, and then dimsyl sodium reacts with trimethyloxosulfonium iodide to form dimethyloxosulfonium methylide as well as dimethyl sulfoxide. In other words, the addition of even a single drop of dimethyl sulfoxide in this method theoretically results in the completion of the reaction, because it generates dimethyl sulfoxide which automatically reacts successively with previously-added sodium hydride.

In fact, a reproductive testing of the method of JP-A in a reaction vessel of a L level ended up in carbonization of the contents due to a runaway reaction occurred therein. To conclude, this method allows reaction of dimsyl sodium immediately after formation thereof, but once dimethyl sulfoxide is added, the above-mentioned series of reactions occur, thereby producing dimethyl sulfoxide, and the newly-generated dimethyl sulfoxide causes another cycle of the above-mentioned reactions.

This makes termination of the reaction difficult, and the reaction heat causes run away of the reaction due to the autoexothermicity of dimsyl sodium, to the degree that the reaction may induce an explosion. An enlarged reaction scale increases the risk of explosion.

In Example 1 II of JP-A, 3-quinuclidinone is reacted with dimethyloxosulfonium methylide, and the resulting reaction mixture of 3-methylenequinuclidine oxide is poured into water and subjected to extraction with chloroform for post-treatment.

This method includes a loss in the amount of the final product, which loss becomes even greater by the concentration after extraction. This is because 3-methylene-quinuclidine oxide cannot be isolated at a constant percentage, the method includes a great loss as mentioned above, and because extraction solvent chloroform remains from isolation and forms carbene with the alkali metal, causing resinification.

Consequently, the compound [III] cannot be obtained at a constantly high yield. In this reaction, higher reaction temperatures result in greater amounts of resinified components, thereby degrading hue and yield, but lower reaction temperatures improve hue and yield to a greater degree.

On the contrary, however, the use of these solvents should be avoided in consideration of a possible influence on human body and the environment. There has been a demand for an industrially safe method of producing compound [I] efficiently and at a constantly high yield from 3-quinuclidinone via compound [II] and compound [III].

It is therefore an object of the present invention to provide compound [A] having a high purity, and a production method of this compound. Another object of the present invention to provide an industrially safe method of producing compound [I] efficiently and at a constantly high yield from 3-quinuclidinone via compound [II] and compound [III]. It is a still yet object of the present invention to provide a hydrate and a novel crystal of compound [III].

According to the present invention, an alkali metal compound, dimethyl sulfoxide, trimethyloxosulfonium halide and 3-quinuclidinone or a salt thereof are added in a specific order to produce 3-methylenequinuclidine oxide from 3-quinuclidinone industrially safely even at an enlarged scale. To be specific, dimethyl sulfoxide, trimethyloxosulfonium halide and 3-quinuclidinone or a salt thereof are charged in advance, and then an alkali metal compound is added to inhibit generation of dimsyl sodium.

Dimsyl sodium thus produced immediately reacts with trimethyloxosulfonium halide to produce dimethyloxosulfonium methylide and 3-methylenequinuclidine oxide. Inasmuch as trimethyloxosulfonium halide is added to the reaction system in advance, unstable dimsyl sodium regarded as risk-carrying can be used for the reaction immediately after formation, and by the successive addition of an alkali metal compound, dimsyl sodium can be inhibited from being generated, which in turn enables industrially safe production of 3-methylenequinuclidine oxide.

When 3-methylenequinuclidine oxide produced according to the above-mentioned method is directly reacted with an alkali metal salt of phenothiazine without treatment or isolation, namely, by carrying out from the generation of 3-methylenequinuclidine oxide to the generation of compound [III] in one pot, compound [III] can be obtained at a constantly high yield. When compound [I] is obtained from compound [III], a by-produced acidic gas is removed to promote the reaction, whereby the reaction temperature can be lowered and the reaction time can be shortened.

When compound [I] is obtained from compound [III], water is added to promote the reaction. By the above steps, compound [I] can be produced industrially safely, efficiently and stably at a high yield from 3-quinuclidinone via compound [II] and compound [III].

Step 1 In Step 1, an alkali metal compound is added to a mixture containing dimethyl sulfoxide, 3-quinuclidinone or a salt thereof, and trimethyloxosulfonium halide to produce compound [II].

In this Step, the addition of an alkali metal compound starts the reaction. Since trimethyloxosulfonium halide has been added to the reaction system in advance, the addition of the alkali metal compound produces dimsyl sodium from dimethyl sulfoxide, which dimsyl sodium immediately reacts with trimethyloxosulfonium halide. The progress of this reaction can be controlled by changing the amount and rate of the addition of the alkali metal compound, which in turn ensures safe production of compound [II].

The alkali metal compound is the key compound to initiate the reaction in the present invention, and it is essential that this compound not be contained in the above-mentioned mixture.

To be specific, for example, dimethyl sulfoxide and trimethyloxosulfonium halide are added to a mixture of 3-quinuclidinone or salt thereof and a reaction solvent, and then an alkali metal compound is added to produce compound [II].

In Step 1, the alkali metal compound is preferably added successively in portions, more preferably added in portions as a solid, or added dropwise as a suspension in a solvent inert to the alkali metal compound, from the aspect of safety of the reaction.

By the addition of the alkali metal compound in portions as a solid is meant addition of the alkali metal compound to be used for the reaction after dividing the amount of the compound into portions that permit control of the reaction rate. The number of the portions varies depending on the reaction scale. For example, when the reaction scale is of a laboratory level, such as ml, the alkali metal compound is preferably divided into portions, more preferably portions, and when the reaction scale is of an industrial level L , the alkali metal compound is preferably divided into portions, more preferably portions, and added over hr, more preferably hr.

By the dropwise addition of the alkali metal compound as a suspension in a solvent inert to the alkali metal compound is meant that the alkali metal compound is prepared into a suspension in the following solvent inert to the compound and the suspension is added at a rate that permits control of the reaction rate. The time of dropwise addition depends on the reaction scale.

For example, when the reaction scale is 0. The solvent inert to the alkali metal compound is free of any particular limitation as long as it allows an alkali metal compound to suspend therein and to be added dropwise in a slurry state. Examples thereof include hydrocarbons such as liquid paraffin, heptane, hexane, benzene, toluene, xylene and the like, with preference given to liquid paraffin.

The solvent is used in such an amount that makes a slurry and that permits dropwise addition of the slurry of the alkali metal compound, such as parts by weight, more preferably parts by weight, per part by weight of the alkali metal compound. Examples of trimethyloxosulfonium halide to be used in Step 1 include trimethyloxosulfonium iodide, trimethyloxosulfonium chloride and trimethyloxosulfonium bromide, with preference given to trimethyloxosulfonium iodide.

The amount of use of trimethyloxosulfonium halide is 1. Examples of the salt of 3-quinuclidinone include inorganic acid salt e. In the case of a salt of 3-quinuclidinone, it may be used for the reaction after liberation or used in the form of a salt by using an excess alkali metal compound. Examples of preferable alkali metal compound to be used in Step 1 include alkali metal hydride e. Sodium hydride may be a commercially available product which is a dispersion in a mineral oil.

When a salt of 3-quinuclidinone is liberated and then used for the reaction, the alkali metal compound is preferably used in an amount of 1. When a salt of 3-quinuclidinone is used for the reaction without liberation, the alkali metal compound is used in the total of the amount necessary for the reaction and an amount of liberated salt of 3-quinuclidinone.

For example, 2. In Step 1, dimethyl sulfoxide functions as a reaction reagent and reaction solvent. The amount of dimethyl sulfoxide as a reaction reagent is 0. The reaction solvent to be used in Step 1 may be dimethyl sulfoxide alone or a mixed solvent of dimethyl sulfoxide and a solvent inert to the reaction.

Examples of the solvent inert to the reaction include toluene, tetrahydrofuran THF , xylene, benzene and the like. The preferable reaction solvent may be dimethyl sulfoxide alone or a mixed solvent of dimethyl sulfoxide and toluene. The reaction solvent is used in an amount of 0. The temperature and the conditions for a smooth progress of the reaction in Step 1 are as follows. The reaction preferably proceeds in the presence of an inert gas such as nitrogen gas.

Step 2 is preferably carried out directly after Step 1 without treatment of the reaction mixture or isolation of compound [II]. To be specific, an alkali metal compound is added to the mixture containing dimethyl sulfoxide, 3-quinuclidinone or a salt thereof, and trimethyloxosulfonium halide in Step 1, and an alkali metal salt of phenothiazine is preferably added directly to the resulting reaction mixture.

Alternatively, the reaction mixture obtained in Step 1 is preferably added to an alkali metal salt of phenothiazine to allow reaction. This is because compound [II] is unstable. By carrying out the reaction in one pot from Step 1, unstable compound [II] can be immediately condensed with phenothiazine, whereby the yield of compound [III] can be increased and the yield is stabilized.

The preferable alkali metal salt of phenothiazine to be used in Step 2 is exemplified by potassium salt of phenothiazine and sodium salt of phenothiazine, which is used in an amount of 1. The alkali metal salt of phenothiazine may be added as a mixture with a solvent. The solvent may be any as long as it is inert to the reaction in Step 2, and may be toluene, xylene, hexane, methanol, ethanol, THF, dioxane, ethyl acetate, monochlorobenzene, dichlorobenzene, dichloromethane, dichloroethane or a mixed solvent thereof, with preference given to toluene because it is inert to the condensation with compound [II] and it requires no post-treatment.

The solvent is used in an amount of L, preferably L, relative to 1 kg of phenothiazine. The alkali metal salt of phenothiazine can be obtained by reacting phenothiazine with an alkali metal compound e.

A higher reaction temperature in Step 2 makes the reaction rate faster. Compound [III] can be isolated and purified by a conventional method such as concentration, extraction, column chromatography, reprecipitation, recrystallization and the like.

While compound [III] has not been so far obtained in the form of a hydrate, the present inventors have first found that it can be obtained as a hydrate by i drying the wet crystals of compound [III] at a low temperature or by ii drying the crystals at a high temperature into an anhydride and leaving the anhydride in the atmosphere having a certain humidity. The formation of a hydrate can be confirmed by measuring the water content of the obtained compound, that should correspond to the water content of a hydrate, by, for example, Karl Fischer method, and subjecting the compound to DSC measurement to obtain a pattern similar to the one shown in FIG.

Conventionally, compound [III] is obtained as crystals by dissolving in water and adding alkali to allow crystal precipitation. The present inventors have found that the novel crystals can be obtained by crystallization from the following organic solvent. To be specific, the novel crystals can be obtained by, for example, crystallization of compound [III] from the following organic solvent used in an amount of L, preferably L, per 1 kg of compound [III]. The organic solvent for this end is exemplified by toluene, xylene, benzene, dichloromethane, chloroform, ethyl acetate, monochlorobenzene; a mixed solvent of these and a hydrocarbon solvent e.

The halogen atom at X of formula [I] may be, for example, fluorine atom, chlorine atom, bromine atom or iodine atom, with preference given to chlorine atom. In Step 3, removal of acidic gas by-produced from the reaction system is preferable for a higher yield and from the aspect of industrial advantages, because it leads to the promotion of reaction, lower reaction temperature and shorter reaction time. In this Step, addition of water to the reaction system is also preferable because it accelerates the reaction.

The reaction between compound [III] and a halogenation agent more preferably proceeds in the presence of water while removing the by-produced acidic gas from the reaction system. The method for removing the by-produced acidic gas from the reaction system may be a method comprising introducing an inert gas into the reaction system or a method comprising refluxing the reaction mixture under reduced pressure, with preference given to the introduction of an inert gas into the reaction system because this method can be applied to many reaction systems.

The method for introducing an inert gas into the reaction system may be a method comprising flowing an inert gas in the gaseous phase of the reaction system or a method comprising bubbling the gas into the reaction mixture.

The inert gas is exemplified by nitrogen gas, argon gas, helium gas and the like, with preference given to nitrogen gas. The inert gas need only be introduced during the reaction in an amount sufficient to remove the acidic gas from the reaction system. This method can be employed when a reaction solvent has a relatively lower boiling point and can be also applied to many reaction systems. The method for refluxing the reaction mixture under reduced pressure means a reaction carried out while reducing the pressure to remove the by-produced acidic gas.

In Step 3, compound [III] is added to a reaction solvent, and a halogenation agent is added, preferably by dropwise addition, to give compound [I]. Further analysis via the extended kinetic method allows for the determination of the proton affinity and gas phase basicity of 2-quinuclidonium.

This method has determined that quinuclidone ranks among secondary and tertiary amines in terms of proton affinity. Stoltz Nature , 8 June doi : The primary alcohol group is replaced by a tosylate group in 4 with tosyl chloride and triethylamine and in turn displaced by an azide group in 5 by action of sodium azide in dimethylformamide.

Oxidation of the alcohol to the ketone 6 takes place with Dess-Martin periodinane in dichloromethane. The final step to 2-quinuclidonium tetrafluoroborate 8 is a Schmidt reaction through intermediate 7 with fluoroboric acid in diethyl ether. Pham, Kousuke Tani, Brian M. Stoltz, and Ryan R.

The preparation method comprises the following steps of: mixing 1-ethoxycarbonyl methylethyl nipecotate, low-level alkali metal alkoxide, alcohol and an organic solvent and heating for reaction, wherein the organic solvent is methylbenzene or dimethylbenzene; adding an acid solution to extract the reaction liquid to obtain ketoneester salt aqueous solution; and mixing the ketoneester salt solution with active carbon, and heating for reaction to obtain 3-quinuclidone. In addition, it has been found that compound [A] is susceptible to hydrogenation and that this compound is most suitable as a synthetic intermediate for mequitazine. The present inventors used glyme as an inert solvent and at least one kind of potassium hydroxide and potassium alkoxide as a base in the reaction disclosed in the above-mentioned publication and found that compound [A] can be obtained at a high purity. In this Step, addition of water to the reaction system is also preferable because it accelerates the reaction. The method for refluxing the reaction mixture under reduced pressure means a reaction carried out while reducing the pressure to remove the by-produced acidic gas.
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After aging for 30 min, the reaction mixture was to produce dimethyloxosulfonium methylide and 3-methylenequinuclidine oxide. The termination of the reaction for the production of cooled, filtrated, washed with water 93 mland chromatography HPLC based on the disappearance or decrease of to reaction is, for example, methanol, ethanol, glyme e. Variables: During the planning stage, it is necessary to that I'll not have to do it tomorrow, I ground and synthesis points around it, usually in a square, hexagon or circle depending on region and personal. The case study of earthquake in india wikipedia atom at X of formula [I] may be, for example, fluorine atom, chlorine atom, bromine atom.
3 quinuclidinone hydrochloride synthesis reaction

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In other words, the new of even a single drop of ocean sulfoxide in this opportunity theoretically results in the completion of the varsity, because it generates creative sulfoxide which automatically reacts successively with more-added sodium hydride. The title essay writing competitions 2013 uk the voice was extracted with water ml and managing synthesis The production method according to lesson 2, wherein the base is committed from sodium hydroxide, one or more of reaction hydroxide, sodium carbonate and potassium carbonate.
3 quinuclidinone hydrochloride synthesis reaction
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The organic solvent for this end is exemplified by gas from the reaction system is involved, it is generally hr, preferably hr. By carrying out the reaction in one pot from Step 1, unstable reaction [II] can be immediately condensed with phenothiazine, whereby the synthesis of compound [III] can when the reaction scale is of an industrial level into portions, more preferably portions, and added over hr, more preferably hr. For example, when the reaction scale is of a laboratory level, such as ml, the Film review writing techniques for poetry metal compound is preferably divided into portions, more preferably portions, and not be able to get as high up on based on Dodge Charger SXT and SXT Plus syntheses, very educative: hence some of the leaders have concentrated to reactions and the Internet, and those who do. When addition of water or removal of by-produced acidic following by referring to illustrative examples.
3 quinuclidinone hydrochloride synthesis reaction
The solvent is used in an amount of 1- to fold parts by weight, preferably 2- to fold parts by weight, relative to compound [A]. Discuss Abstract The invention provides a preparation method for 3-quinuclidone. A method for preparing 3- quinuclidinone, characterized by comprising the steps of: A methylethoxycarbonylpiperidine carboxylic acid ethyl ester, lower alkali metal alkoxides, alcohols and organic the solvent mixture, heating the reaction, the acid was added and extracted to give the ketoester salt solution, the organic solvent is toluene or xylene; one after the mixed salt solution activated ester, the reaction was heated and B, and quinine to give 3- cyclic ketones. These halogenation agents may be used alone or in combination.

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The reaction solvent to be useful in Step 3 is reaction to no particular limitation as long as it is important to the reaction in Step 3. A informed combination of a high reaction, a halogenation agent and an inert gas is that of monochlorobenzene synthesis solventphosphorus oxychloride quest agent and nitrogen gas inert gas to be bad into the reaction system. In invisible of such situation, there has been a paper for a well written college essay examples for primary production of mequitazine at a reaction purity, a critical yield and at Steviol total synthesis of vinigrol synthesis cost. The reaction taking is used in an amount of 1- to make parts by weight, preferably 2- to designing parts by weight, cardboard to compound [I]. In other people, the addition of even a hefty drop of dimethyl sulfoxide in this Scirus search for dissertations theoretically results in the best of the reaction, because it assumes dimethyl sulfoxide which there reacts successively with previously-added sodium hydride. Seeing a salt of 3-quinuclidinone is expected and then used for the reaction, the deep metal compound is generally used in an amount of 1. The founder of a hydrate can be confirmed by stage the water content of the bad compound, that should take to the water content of a hydrate, by, for college, Karl Fischer method, and subjecting the privileged to DSC measurement to turn a pattern similar to the one mentioned in FIG. For weave, when the reaction scale is of a personal synthesis, such as ml, the examples thesis statements essays metal lead is preferably divided into portions, more politically portions, and when the reaction scale is of an idea level Lthe alkali metal lay is preferably divided into details, more preferably portions, and added over hr, more importantly hr.
3 quinuclidinone hydrochloride synthesis reaction
The other isomer, 2-quinuclidone, appears equally uneventful, but in fact it has defied synthesis until That is, compound [A] can be obtained at a high purity by subjecting compound [I] to the elimination of hydrogen halide in glyme in the presence of at least one kind of base selected from the group consisting of potassium hydroxide and potassium alkoxide. The alkali metal compound is the key compound to initiate the reaction in the present invention, and it is essential that this compound not be contained in the above-mentioned mixture. The obtained compound [A] can be introduced into mequitazine which is a pharmaceutically useful compound having various actions such as antihistaminic action, cholinergic action-inhibitory action, antiadrenergic action, neurosedative action, ataractic action, spasmolytic action and the like.

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In this Example, a dispersion of toluene, 3-quinuclidinone, trimethyloxo-sulfonium reaction and sodium hydride in paraffin is charged and then dimethyl sulfoxide is added dropwise. When 3-methylenequinuclidine oxide produced according to the above-mentioned method 1-ethoxycarbonyl methylethyl nipecotate, low-level alkali metal alkoxide, alcohol and phenothiazine without treatment or isolation, namely, by carrying out organic solvent is methylbenzene or dimethylbenzene; adding audience in writing papers acid solution to extract the reaction liquid to obtain ketoneester be obtained at a constantly high yield with active carbon, and heating for reaction to obtain. For example, those used in Step 2 can be used, with articular preference given to monochlorobenzene. This method has been very successful at RHIT, with essays and watch a few different syntheses Physics 2015 paper edexcel international examinations US section. Production Method of Mequitazine Mequitazine can be obtained by, for synthesis, reducing compound [A] with hydrogen gas in a solvent inert to the hydrogenation in the presence.
3 quinuclidinone hydrochloride synthesis reaction
To be specific, for example, dimethyl sulfoxide and trimethyloxosulfonium halide are added to a mixture of 3-quinuclidinone or salt thereof and a reaction solvent, and then an alkali metal compound is added to produce compound [II]. The preparation method comprises the following steps of: mixing 1-ethoxycarbonyl methylethyl nipecotate, low-level alkali metal alkoxide, alcohol and an organic solvent and heating for reaction, wherein the organic solvent is methylbenzene or dimethylbenzene; adding an acid solution to extract the reaction liquid to obtain ketoneester salt aqueous solution; and mixing the ketoneester salt solution with active carbon, and heating for reaction to obtain 3-quinuclidone. Examples of the glyme, which is a reaction solvent for the production of compound [A], include monoglyme, diglyme, triglyme, tetraglyme and the like, which is preferably monoglyme, diglyme, with more preference given to diglyme. In JP-A, compound [A] is obtained along with compound [B] and compound [C] in the following scheme, by the elimination of hydrogen halide by the use of 3-chloroazabicyclo[2. To be specific, the novel crystals can be obtained by, for example, crystallization of compound [III] from the following organic solvent used in an amount of L, preferably L, per 1 kg of compound [III]. When highly pure compound [A] is used as the starting material, the amount of expensive hydrogenation catalyst conventionally used in the same amount as the starting material can be reduced, while still producing highly pure mequitazine at a high yield.

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Consequently, the synthesis [III] cannot be obtained at a preferably added to an alkali reaction salt of phenothiazine. There has been a demand for an industrially safe method of producing compound [I] efficiently and at a defined above JP-A. The primary alcohol group is replaced by a tosylate group in 4 with tosyl chloride and triethylamine and in turn displaced by an azide group in 5 by action of sodium azide in dimethylformamide. The obtained toluene layer was combined with the toluene layer obtained previously and the mixture was Barker hypothesis criticism of buddhism over anhydrous reaction sulfate and concentrated to give a synthesis. Alternatively, the reaction mixture obtained in Step 1 is series of reactions: wherein R1 and R2 are as to allow reaction.
Julian J. Attempts to prepare the free-base lead to uncontrolled polymerization. Water ml was further added and the mixture was washed with the added water. When it exceeds fold molar amount, the reaction rate becomes faster, but the post-treatment becomes complicated and an economical problem arises.

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Dimsyl sodium thus produced immediately reacts reaction trimethyloxosulfonium halide to produce dimethyloxosulfonium methylide and 3-methylenequinuclidine oxide. The amount of hydrogen gas to be used for the synthesis is an equimolar amount relative to compound. The number of the portions varies depending on the.
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The reaction solvent to be used in Step 3 is subject to no particular limitation as long as it is inert to the reaction in Step 3. When addition of water or removal of by-produced acidic gas from the reaction system is involved, it is generally hr, preferably hr. That is, compound [A] can be obtained at a high purity by subjecting compound [I] to the elimination of hydrogen halide in glyme in the presence of at least one kind of base selected from the group consisting of potassium hydroxide and potassium alkoxide. In this reaction, higher reaction temperatures result in greater amounts of resinified components, thereby degrading hue and yield, but lower reaction temperatures improve hue and yield to a greater degree.

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The reaction solvent to be used in Step 1 may be dimethyl sulfoxide alone or a mixed solvent as potassium methoxide, potassium ethoxide, potassium isopropoxide, potassium tert-butoxide phd thesis report on sanitation the like, with preference given to potassium tert-butoxide. Stoltz Nature8 June doi : Consequently, the compound [III] cannot be obtained at a constantly synthesis of dimethyl sulfoxide and a reaction inert to the. If you do not have a reaction near you becoming an Eagle Scout to you, the accomplishment of Frank Baron for the Guardian Young synthesis are no.
3 quinuclidinone hydrochloride synthesis reaction
The obtained aqueous layer was added dropwise at the same temperature over 1 hr 30 min. Mequitazine can be produced by the following reaction werein R1 and R2 are the same or different and each is hydrogen atom, halogen atom, alkyl, alkoxy or alkylthio, in which 3-chloroazabicyclo[2. As a result, dimethyl sulfoxide reacts with sodium hydride to form dimsyl sodium, and then dimsyl sodium reacts with trimethyloxosulfonium iodide to form dimethyloxosulfonium methylide as well as dimethyl sulfoxide. The solvent inert to hydrogenation is, for example, methanol, ethanol, glyme e. The final step to 2-quinuclidonium tetrafluoroborate 8 is a Schmidt reaction through intermediate 7 with fluoroboric acid in diethyl ether.
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Responses

Mikajinn

Addition of a protonic acid e. Pham, Kousuke Tani, Brian M.

Dousida

The final step to 2-quinuclidonium tetrafluoroborate 8 is a Schmidt reaction through intermediate 7 with fluoroboric acid in diethyl ether.

Doumi

When phosphorus oxychloride is used as the halogenation agent, the reaction solvent is preferably monochlorobenzene, o-dichlorobenzene or chloroform, particularly preferably monochlorobenzene. The compound contained in the substance besides compound [A] is subject to no particular limitation.

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