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Compounding method for racecadotril intermediate

A racecadotril and synthesis method technology, applied in the field of drug synthesis, can solve the problems of unfavorable industrial production, production environmental pollution, long synthetic route, etc., and achieve the effects of easy industrial production, high purity and high product yield

Active Publication Date: 2017-03-29
SHANDONG BOYUAN PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The above-mentioned synthesis route is relatively long, and the raw material benzyl chloride with great toxicity and irritation is used, which easily causes great pollution to the production environment, brings huge pressure to environmental protection, and has high production cost, which is not conducive to industrial production

Method used

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  • Compounding method for racecadotril intermediate
  • Compounding method for racecadotril intermediate
  • Compounding method for racecadotril intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] (1) Add 70g of ethyl phenylpropionate and 400ml of ethyl acetate to a 1000ml reaction bottle, stir evenly, cool down, control the temperature in the reaction bottle at 0-10°C, add 54.7g of dimethylamine with a concentration of 40% dropwise, and the addition is completed , and react at a temperature of 10-15°C for 1 hour, then add 14.2g of paraformaldehyde, heat up and then reflux for 3 hours; after the reaction is completed, cool down to room temperature, add 56g of concentrated hydrochloric acid (concentration 35%, the same below) and 60ml of purified water, Stir for 40 minutes, stand to separate layers, wash the organic layer once with 200ml purified water, and concentrate the organic layer to dryness under reduced pressure;

[0025] (2) Then add 500ml of dichloromethane, 80g of 20% sodium hydroxide solution and 50g of absolute ethanol, and react at a temperature of 10-20°C for 4 hours; pH=1; separate the water layer again, wash the organic layer with 300ml of purifie...

Embodiment 2

[0027] (1) Add 70g of ethyl phenylpropionate and 400ml of ethyl acetate to a 1000ml reaction bottle, stir evenly, cool down, control the temperature in the reaction bottle at 0-10°C, add 55.0g of dimethylamine with a concentration of 40% dropwise, and the addition is completed , temperature control 10-15 ℃ for 50 minutes, then add 14.5g of paraformaldehyde, heat up and then reflux for 2.5 hours; after the reaction is completed, cool down to room temperature, add 58g of concentrated hydrochloric acid (concentration 35%), 65ml of purified water, and stir for 40 minutes , standing to separate layers, the organic layer was washed once with 200ml purified water, and the organic layer was concentrated under reduced pressure to dryness;

[0028] (2) Then add 500ml of methylene chloride, 85g of 20% sodium hydroxide solution and 50g of absolute ethanol, and react at a temperature of 10-20°C for 3.5 hours; after standing, separate the water layer, and add 45g of concentrated hydrochloric...

Embodiment 3

[0030] (1) Add 70g of ethyl phenylpropionate and 400ml of ethyl acetate to a 1000ml reaction bottle, stir evenly, cool down, control the temperature in the reaction bottle at 0-10°C, add 54.5g of dimethylamine with a concentration of 40% dropwise, and the addition is completed , and react at a temperature of 10-15°C for 70 minutes, then add 14.0g of paraformaldehyde, heat up and then reflux for 3.5 hours; after the reaction is completed, cool down to room temperature, add 55g of concentrated hydrochloric acid (concentration 35%), 60ml of purified water, and stir for 40 minutes , standing to separate layers, the organic layer was washed once with 200ml purified water, and the organic layer was concentrated under reduced pressure to dryness;

[0031] (2) Then add 500ml of dichloromethane, 80g of 20% sodium hydroxide solution and 50g of absolute ethanol, and react at a temperature of 10-20°C for 4 hours; pH=1; separate the water layer again, wash the organic layer with 300ml of p...

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Abstract

The invention discloses a compounding method for a racecadotril intermediate. The compounding method comprises the following steps: causing ethyl phenylpropiolate, dimethylamine and trioxymethylene react with each other, treating with hydrochloric acid to obtain benzyl ethyl acrylate, and then hydrolyzing under an alkaline condition, thereby obtaining benzyl acrylic acid. According to the compounding method disclosed by the invention, benzyl chloride with higher toxicity is replaced by ethyl phenylpropiolate, the compounding route is shortened, the production efficiency is increased, and thus the compounding method is suitable for industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing a racecadotril intermediate, belonging to the technical field of drug synthesis. Background technique [0002] Racecadotril is an anti-diarrhea drug with a new mechanism of action, which directly inhibits excessive intestinal secretion and rapidly improves diarrhea symptoms. It is suitable for acute diarrhea in adults and infants and children over 1 month old. Racecadotril was first successfully developed by the French Bioprojet company. It was first listed in France under the trade name Tiorfan in 1993. Soon after it went on the market, the Canadian Pediatric Association and the US Centers for Disease Control and Prevention (CDC) included racecadotril in the list. In 2011, it was also included in the recommended drugs of the Chinese National Pediatric Diarrhea Treatment Consensus. At present, domestic front-line pediatricians have regarded racecadotril as an efficient and safe drug for the clinical ...

Claims

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Application Information

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IPC IPC(8): C07C27/02C07C51/42C07C57/42C07C67/343C07C69/618
CPCC07C51/09C07C51/42C07C67/343C07C57/42C07C69/618
Inventor 赵孝杰张敏刘远慧
Owner SHANDONG BOYUAN PHARM CO LTD
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