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Synthesis method of process impurity of amisulpride

A kind of technology of amisulpride and synthesis method, applied in directions such as organic chemistry

Pending Publication Date: 2021-07-02
BEIJING VENTUREPHARM BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] After retrieval, there is no bibliographical report of this impurity synthesis, therefore, providing a kind of synthetic method of amisulpride magazine is used for the preparation of impurity standard substance has important practical significance

Method used

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  • Synthesis method of process impurity of amisulpride
  • Synthesis method of process impurity of amisulpride

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Experimental program
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Embodiment 1

[0017] Dissolve 5.0g of N-ethyl-2-aminomethylpyrrolidine in 50ml of ethyl acetate, add 10.2g of (BOC) 2 O was stirred at room temperature for 0.5h, and then heated to 20°C for 2h. The reaction solution was washed with 40 ml of water, and the organic solvent was removed by rotary evaporation twice. To obtain tert-butyl 1-ethylpyrrolidine-2-methylcarbamate (3), dissolve the product in 50ml of DMF, add 1.87g of NaH, stir at room temperature for 1h and then add CH 3 6.6g of I solution was stirred for 0.5h, then warmed up to 20°C and stirred for 2h, cooled to room temperature, added 20ml of water to quench the reaction, and then separated, and the solvent was removed by rotary evaporation to obtain N-(1-ethylpyrrolidin-2-methyl ), N-methylcarbamate tert-butyl ester, the product was dissolved in 20ml of 50% trifluoroacetic acid and 20ml of dichloroethane solution and stirred for 1h. Liquid separation and rotary evaporation to remove the organic phase to obtain N-ethyl-2-methylamin...

Embodiment 2

[0019] Dissolve 5.0 g of N-ethyl-2-aminomethylpyrrolidine in 50 ml of methylene chloride, add 10.2 g of (BOC) 2 O was stirred at room temperature for 0.5h, then heated to 60°C for 2h. The reaction solution was washed with 40 ml of water, and the organic solvent was removed by rotary evaporation twice. To obtain tert-butyl 1-ethylpyrrolidine-2-methylcarbamate (3), dissolve the product in 50ml of tetrahydrofuran, add 1.87g of NaH, stir at room temperature for 1h, and then add 4.2g of dimethyl carbonate solution After stirring for 0.5h, the temperature was raised to 50°C and stirred for 2h, then cooled to room temperature, and 20ml of water was added to quench the reaction, and the liquid was separated, and the solvent was removed by rotary evaporation to obtain N-(1-ethylpyrrolidine-2-methyl),N- For tert-butyl methylcarbamate, dissolve the product in a solution of 20ml of 1.5M hydrochloric acid and 20ml of dioxane and stir for 1h. Liquid separation and rotary evaporation to re...

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Abstract

The invention discloses a synthesis method of a process impurity of amisulpride, and belongs to the technical field of chemical pharmacy. N-ethyl-2-aminomethylpyrrolidine (2) reacts with (BOC)2O to obtain 1-ethyl pyrrolidine-2-methyl tert-butyl carbamate (3); CH3I is added under the alkaline condition of NaH, and methylation is performed to obtain N-(1-ethyl pyrrolidine-2-methyl), N-methyl tert-Butyl carbamate (4); under an acidic condition, hydrolysis is carried out to obtain N-ethyl-2-methylaminomethylpyrrolidine (5); and finally reaction with 4-amino-5-(ethylsulfonyl)-2-methoxybenzoic acid (6) is performed under the catalysis of theorganic alkali N',N-carbonyldiimidazole (CDI) to obtain an amisulpride impurity (1). The synthesized high-purity amisulpride impurity is used as an impurity standard substance in detection and analysis ofamisulpride finished products, so that the positioning accuracy of the amisulpride impurity is improved; control on impurities is enhanced, and the purpose of controlling the quality of the finished amisulpride is finally achieved; and the raw materials are simple and easy to obtain, and operation is simple.

Description

technical field [0001] The invention discloses a synthesis method of a process impurity of amisulpride, belongs to the technical field of chemical pharmacy, and relates to a 4-amino-N-[(1-ethyl-2-pyrrolidinyl)methyl]-N -The synthetic method of [methyl]-5-(ethylsulfonyl)-2-methoxybenzamide. Background technique [0002] Amisulpride is a broad-spectrum antipsychotic drug developed by Sanofi Synthelabo, France, and is widely used in adult schizophrenic patients with acute and chronic, positive and negative symptoms. It was launched in January 1997 Available in the US, its patent expired in 2008, and it's sold in every English-speaking country except Canada and the US. Launched in China in 2001, it has become the first-line drug for the treatment of acute progressive and chronic schizophrenia. [0003] There are two companies that have been approved to manufacture amisulpride in China, namely Qilu Pharmaceutical Co., Ltd. and Sanofi-Sindela Fort Pharmaceutical Company. Judging...

Claims

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Application Information

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IPC IPC(8): C07D207/09
CPCC07D207/09
Inventor 吴边边赵国磊
Owner BEIJING VENTUREPHARM BIOTECH
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