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New synthesis process of sultopride hydrochloride

A technology of sultapride hydrochloride and hydrochloric acid, which is applied in the new synthesis field of anti-schizophrenia drug sutopride hydrochloride, can solve the problems of complicated post-processing, difficult recovery, and no practical value, and achieves stable yield and easy operation. , the effect of greatly improving

Active Publication Date: 2005-12-14
JIANGSU TASLY DIYI PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The post-treatment of this method is complicated, and a large amount of solvents such as pyridine and chloroform are used, and it is not easy to recycle, and the yield is only 44.9%, so there is no practical value in production

Method used

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  • New synthesis process of sultopride hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] (1) Preparation of 2-methoxy-5-ethylsulfonylbenzoic acid methyl ester

[0047] In a dry three-necked flask, first drop methanol (385ml), then slowly add concentrated sulfuric acid (38ml) under stirring, control the temperature to be less than 30°C, and finally add 2-methoxy-5-ethanesulfonylbenzoic acid ( 100g); after addition, stir and heat to reflux, react for 4hrs, place it under cooling, suction filter, wash with water until neutral, and obtain white crystal 2-methoxy-5-ethylsulfonylbenzoic acid methyl ester (91.5g), melting point 126.5 -128°C, yield 86.5%.

[0048] (2) preparation of sultopride hydrochloride

[0049] In a 500ml three-necked flask, put ethylene glycol (135ml) first, and then put N-ethyl-2-aminomethyltetrahydropyrrolidine (33.5ml) and 2-methoxy-5-ethanesulfonate successively under stirring. Methyl acylbenzoate (50g); after the injection, heat to 80±5°C and keep it warm for 10hrs. After the reaction, cool to room temperature, then acidify with hydroc...

Embodiment 2

[0051] (1) Preparation of 2-methoxy-5-ethylsulfonylbenzoic acid methyl ester

[0052] In a dry there-necked flask, first drop methanol (500ml), then slowly add concentrated sulfuric acid (50ml) under stirring, control the temperature below 30°C, and finally add 2-methoxy-5-ethanesulfonylbenzoic acid ( 125g); after addition, stir and heat to reflux, react for 4hrs, cool and place, suction filter, wash with water to neutrality, and obtain white crystal 2-methoxy-5-ethylsulfonylbenzoic acid methyl ester (118.4g), melting point 126.5 -128°C, yield 89.6%.

[0053] (2) preparation of sultopride hydrochloride

[0054] In a 500ml three-necked bottle, put glycerin (55ml) first, then put N-ethyl-2-aminomethyltetrahydropyrrolidine (67ml) and 2-methoxy-5-ethanesulfonylbenzoic acid in turn under stirring Methyl ester (100g); after the injection, heat to 95±5°C and keep it warm for 6hrs. After the reaction, cool to room temperature, then acidify with hydrochloric acid to pH=1 to obtain of...

Embodiment 3

[0056] (1) Preparation of 2-methoxy-5-ethylsulfonylbenzoic acid methyl ester

[0057]In a dry three-necked flask, first drop methanol (400ml), then slowly add concentrated sulfuric acid (40ml) under stirring, control the temperature below 30°C, and finally add 2-methoxy-5-ethanesulfonylbenzoic acid ( 100g); after adding, stir and heat to reflux, react for 4hrs, place it under cooling, filter with suction, wash with water until neutral, and obtain white crystal 2-methoxy-5-ethylsulfonylbenzoic acid methyl ester (93g), melting point 126.5- 128°C, yield 88%.

[0058] (2) preparation of sultopride hydrochloride

[0059] In a 500ml three-necked flask, put ethylene glycol (135ml) first, and then put N-ethyl-2-aminomethyltetrahydropyrrolidine (33.5ml) and 2-methoxy-5-ethanesulfonate successively under stirring. Methyl acylbenzoate (50g); after throwing in, heat to 90±5°C and keep it warm for 7hrs. After the reaction, cool to room temperature, then acidify with hydrochloric acid to ...

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Abstract

The present invention relates to the new synthesis process of sultopride hydrochloride. The synthesis process includes the following steps: 1. the reaction between 2-methoxy-5-ethanesulbonyl benzoic acid and methanol to produce 2-methoxy-5-ethanesulbonyl methyl benzoate; 2. the reaction between 2-methoxy-5-ethanesulbonyl methyl benzoate obtained in the step 1 and N-ethyl-2-aminomethyl tetrahydropirrolidine to produce sultopride; and 3. the reaction between sultopride and hydrochloric acid to obtain sultopride hydrochloride.

Description

Technical field: [0001] The invention relates to a novel synthesis method of sultopride hydrochloride, an antipsychotic drug. Background technique: [0002] Sultopride Hydrochloride (Sultopride Hydrochloride, 1), the chemical name is N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-(ethylsulfonyl)-2-methoxybenzenesulfonate Amide hydrochloride, a drug used for the control of acute schizophrenia, can control mental agitation, agitation and behavioral disorders, was developed and marketed by the French company Delagrange in 1989. Bibliography reports that the synthetic method of sultopride hydrochloride all is to be raw material with 2-methoxy group-5-ethanesulfonyl benzoic acid, and one method is first chlorination, rear condensation, acidification salt make finished product, and its shortcoming is chlorine The chemical reaction is not easy to operate, the chlorination product is unstable, and the yield is low. Another method is to directly condense N-ethyl-2-aminomethyltetrahydropyrrol...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/09
Inventor 朱占元杨国军
Owner JIANGSU TASLY DIYI PHARMA CO LTD
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