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Preparation method of key intermediate of roxatidine acetate hydrochloride

A technology of roxatidine hydrochloride acetate and intermediates, which is applied in the field of drug synthesis, can solve the problems of flammable and explosive safety hazards, complex requirements for industrial equipment, and high production costs, so as to reduce production costs and reduce equipment costs. Requirements, energy saving effect

Inactive Publication Date: 2015-01-28
哈药集团人民同泰医药股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although this route is relatively mature, the reaction conditions for the synthesis of 3 steps from 2 are high temperature above 180°C, decompression and dehydration, which not only requires complicated industrial equipment, but also consumes a lot of energy, and the operation is difficult to control, which increases the production cost. There are great potential safety hazards of flammability and explosion, and it has been a technical problem that has plagued production enterprises for many years.

Method used

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Examples

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Effect test

Embodiment 1

[0019] Example 1: Prepare 15 mL of anhydrous chloroform mixed solution containing 0.29 g of DMAP and 2.61 g of DCC for future use. Add 3.0 g of 3-piperidinylmethyl-phenoxypropylamine (I), 1.02 g of glycolic acid and 15 mL of anhydrous chloroform into the three-necked flask, and stir to dissolve. Add the prepared DMAP-DCC mixture dropwise under ice-water bath. After the dropwise addition, the mixture was stirred in an ice-water bath for 30 minutes, and then reacted at room temperature for 4 hours.

[0020] The reaction solution was filtered. Add 60 mL of water to the filtrate, stir well and filter, and discard the aqueous phase, repeat three times. Add 60 mL of water to the organic phase, adjust the pH to 4-5 with acetic acid, and separate the liquids after standing still. The pH of the aqueous phase was adjusted to 9-10 with aqueous ammonia, and extracted three times with 40 mL of chloroform. The organic phase was washed with 40 mL of water, dried with anhydrous magnesium ...

Embodiment 2

[0021] Example 2: Prepare 15 mL of anhydrous dichloromethane mixed solution containing 0.29 g of DMAP and 2.32 g of EDC for subsequent use. Add 3.0 g of 3-piperidinyl-phenoxypropylamine (I), 1.02 g of glycolic acid, and 15 mL of anhydrous dichloromethane into the three-necked flask, and stir to dissolve. Add the prepared DMAP-EDC mixture dropwise under ice-water bath. After the dropwise addition, the mixture was stirred in an ice-water bath for 30 minutes, and then reacted at room temperature for 4 hours.

[0022] The reaction solution was filtered. Add 60 mL of water to the filtrate, stir well and filter, and discard the aqueous phase, repeat three times. Add 60 mL of water to the organic phase, adjust the pH to 4-5 with acetic acid, and separate the liquids after standing still. The pH of the aqueous phase was adjusted to 9-10 with aqueous ammonia, and extracted three times with 40 mL of dichloromethane. The organic phase was washed with 40 mL of water, dried with anhydr...

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Abstract

The invention provides a preparation of a key intermediate N-{3-[3-(1-piperidylmethyl)phenoxyl]propyl}hydroxyacetamide of roxatidine acetate hydrochloride. The method has the advantages of safe reaction, mild conditions, simple process, high product purity and industrialization benefiting. The problems of strict preparation conditions, very high requirements on industrial devices, energy consumption and operation control, severs hidden safety troubles and the like of traditional methods are solved.

Description

technical field [0001] The invention relates to a preparation method of N-{3-[3-(1-piperidinemethyl)phenoxy]propyl}hydroxyacetamide, a key intermediate of synthetic chemical raw material drug roxatidine acetate hydrochloride, belonging to the field of drug synthesis. Background technique [0002] Roxatidine acetate hydrochloride is a fourth-generation H2 receptor antagonist and an excellent anti-ulcer drug. For the treatment of upper gastrointestinal bleeding caused by peptic ulcer, stress ulcer, and hemorrhagic gastritis. After listing, it quickly occupied the market with its outstanding advantages such as significant clinical efficacy, rapid onset of effect, low side effects, and good tolerance. [0003] At present, most of the synthetic techniques of roxatidine hydrochloride acetate adopt m-hydroxybenzaldehyde as starting raw material, and obtain product through four-step reaction, and reaction route is as formula one: [0004] Although this route is relatively mature,...

Claims

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Application Information

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IPC IPC(8): C07D295/096
CPCC07D295/096
Inventor 刘春凤秦雅英范宁张晓霞王敬伟
Owner 哈药集团人民同泰医药股份有限公司
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