Synthesis method of itopride hydrochloride

A technology of itopride hydrochloride and a synthesis method is applied in the synthesis field of itopride hydrochloride, and can solve the problem of not conforming to the concept of green and safe pharmaceutical production, tedious preparation of ethoxybenzylamine, and low total yield of the synthesis process and other problems to achieve the effect of reducing production risks, reducing production and raw material costs, and reducing production costs

Inactive Publication Date: 2018-04-10
安徽修一制药有限公司
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Problems solved by technology

However, the preparation of the key intermediate 4-{2-(dimethylamino)}ethoxybenzylamine is cumbersome, and the steps are long, and the dangerous process of pressurized hydrogenation of Raney gold must be carried out, and the purity of the obtained product is 95 %, it is more difficult to purify, and then also leads to the decrease of t

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  • Synthesis method of itopride hydrochloride
  • Synthesis method of itopride hydrochloride

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Embodiment 1

[0020] (1) Preparation of N-(4-hydroxy)benzyl-3,4-dimethoxybenzamide:

[0021] 200 g of p-hydroxybenzylamine and 326 g of 3,4-dimethoxybenzoyl chloride were put into a dry reaction flask containing 1000 ml of dichloromethane. 129g of pyridine was carefully added under stirring at room temperature, heated to reflux for 2h, the reaction was completed, after the solvent was evaporated, the residue was washed with water and dried to obtain a yellow solid product, weight 448g, purity 98%. The yield is 95%.

[0022] (2) Preparation of Itopride Hydrochloride:

[0023] Put 448g of the obtained amide product and 260g of 2-chloro-N,N-dimethylethylamine into a dry reaction flask containing 1300ml DMF, then put in 2.6g potassium iodide, stir and raise the temperature to 130-135°C, and react for 8-10h. After the reaction was completed, after the solvent was evaporated under reduced pressure, 1200ml of absolute ethanol was put into the bottle, and after stirring to dissolve, 8ml of 30% hydrochlo...

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Abstract

The invention discloses a synthesis method of itopride hydrochloride, and relates to the technical field of organic synthesis. Hydroxybenzylamine is taken as starting material, in non-polar solvent, in the presence of an acid-binding agent, the Hydroxybenzylamine and 3,4-dimethoxybenzoyl chloride are subjected to amidation to obtain an intermediate N-(4-hydroxyl) benzyl-3,4-dimenthoxybenzamide, and in polar solvent, in the presence of a catalyst, the intermediate N-(4-hydroxyl) benzyl-3,4-dimenthoxybenzamide and 2-chlorine-N,N-dimethylethylamine are subjected to etherification to obtain the itopride hydrochloride. According to the method, the raw materials are easy to obtain, the route is short, only two steps of synthetic reactions are needed, the high yield of 85-97% can be achieved in each step, by means of amidation and etherification with high product purity, a dangerous process of high-pressure hydrogenation is avoided successfully, and meanwhile, the production and raw materialcosts are greatly reduced.

Description

Technical field: [0001] The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing itopride hydrochloride. Background technique: [0002] Itopride hydrochloride is a new type of drug developed by Hokuriku Pharmaceutical Co., Ltd. to promote gastrointestinal motility. It is mainly used clinically to treat various dyspeptic symptoms caused by non-ulcer dyspepsia and chronic gastritis, with low side effects It is a real gastrointestinal motility agent without serious reactions of similar drugs. [0003] At present, the synthetic methods of itopride hydrochloride are based on 4-(2-dimethylamino)ethoxy)benzylamine and 3,4-dimethoxybenzoyl chloride as key intermediates, which occur in a solvent. Amidation reaction. However, the preparation of the key intermediate 4-{2-(dimethylamino)} ethoxybenzylamine is relatively cumbersome, the steps are longer, and the dangerous process of pressure hydrogenation of Ranisin must be carried out. The...

Claims

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Application Information

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IPC IPC(8): C07C231/12C07C235/48
CPCC07C231/02C07C231/12C07C235/48
Inventor 董来山刘忠平何长林
Owner 安徽修一制药有限公司
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