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A kind of preparation method of itopride hydrochloride

A technology of itopride hydrochloride and hydrochloride is applied in the field of preparation of gastrointestinal prokinetic drug itopride hydrochloride, which can solve the problem of high cost and achieve the effects of easy purchase, sufficient market supply and low price

Active Publication Date: 2018-04-17
迪嘉药业集团股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method starting material p-fluorobenzaldehyde and palladium charcoal reduction cause the cost of final product to be higher

Method used

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  • A kind of preparation method of itopride hydrochloride
  • A kind of preparation method of itopride hydrochloride
  • A kind of preparation method of itopride hydrochloride

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Embodiment 1

[0028] Step 1: Add 94g (1mol) of phenol and 117.6g (2.1mol) of potassium hydroxide to 600ml of ethanol and stir to dissolve, control the temperature at 55-60°C and slowly add N,N-dimethyl chloride ethyl salt Salt 158g (1.1mol, dissolved in 300g water), after the dropwise addition, the reaction was continued for 4 hours; after the reaction was completed, ethanol was recovered, and dichloromethane was added to extract twice, combined, washed with water, and concentrated to obtain 142g oil XI, yield 86.0 %;

[0029] Step 2: Stir and dissolve 132g (0.8mol) of oil XI and 195g (1.6mol) of 30% concentrated hydrochloric acid in 400ml of water, keep the temperature below -10°C, add 24g (0.8mol) of paraformaldehyde in 4 batches, Continue the reaction for 10 hours; TLC monitors the completion of the reaction, adjust the pH to 8-9 with sodium carbonate, add dichloromethane to extract twice, combine the organic phases, concentrate to obtain an oil, then add 300ml of ethyl acetate to dissol...

Embodiment 2

[0034] Step 1: Add 94g (1mol) of phenol and 84g (2.1mol) of sodium hydroxide to 600ml of ethanol, stir and dissolve, control the temperature at 55-60°C, and slowly drop N,N-dimethylchloroethane hydrochloric acid 158g of salt (1.1mol, dissolved in 300g of water), the dropwise addition was completed and the reaction continued for 4 hours; after the reaction was completed, ethanol was recovered, and dichloromethane was added to extract twice, combined, washed with water, and concentrated to obtain 136g of oil XI, with a yield of 82.4% ;

[0035] Step 2: Stir and dissolve 132g (0.8mol) of oil XI and 195g (1.6mol) of 30% concentrated hydrochloric acid in 400ml of water, keep the temperature below -10°C, and slowly add 40g (0.8mol) of 40% formaldehyde solution dropwise , and continued to react for 2 hours; TLC monitored the completion of the reaction, adjusted the pH to 8-9 with sodium carbonate, added dichloromethane to extract twice, combined the organic phases, concentrated to ob...

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Abstract

A kind of preparation method of itopride hydrochloride The present invention relates to the preparation method of itopride hydrochloride, the reaction takes 2-dimethylaminochloroethane hydrochloride and phenol as starting materials, through etherification, chloromethylation , amino substitution, amidation, and salt-forming 5-step reaction to obtain itopride hydrochloride. In the present invention, the chloromethylation promoted by HCl / CHO avoids the imine reduction step, eliminates the solid waste generated by the reducing agent, and improves the safety of the reaction; the raw materials used are cheap, the market supply is sufficient, and they are easy to purchase; The one-step reaction is more classic, safe and easy to control, and suitable for industrial production.

Description

technical field [0001] The invention relates to the preparation of itopride hydrochloride, a gastrointestinal prokinetic drug. Background technique [0002] Itopride hydrochloride is a new generation of gastrointestinal motility drug for the treatment of functional dyspepsia. Through comparison of treatment effects, itopride hydrochloride is significantly better than domperidone in treating belching, decreased food intake, and early satiety. For details, see Ma Qiaoling, Zhang Shaomei, Wen Shuangshuang; Qilu Pharmaceutical Affairs, 2004, 23(1), 51-52. [0003] The synthesis of itopride hydrochloride can be roughly divided into the following routes: [0004] (1) Amide method [0005] [0006] Both US2009177008 and WO200774386 adopt this route. Using 3,4-dimethoxybenzoyl chloride I and p-hydroxybenzylamine II as starting materials, the amide intermediate III is first prepared, and then combined with N,N-dimethylaminoethyl Chlorohydrochloride IV is reacted to give itoprid...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C235/48C07C231/02C07C231/12
Inventor 吴荣贵姜凯安冬华崔仰仰门连彬
Owner 迪嘉药业集团股份有限公司
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