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Preparation method of 3-[(1-(1S)-phenylethyl) amino]-2,3,4,5-tetrahydro-2-oxo-1H-(3S)-benzazepine

A technology of phenethyl and benzonitride, applied in the field of compound preparation, can solve problems such as high cost, difficulty, low yield, etc., and achieve the effects of easy industrial implementation and simple operation

Active Publication Date: 2011-11-23
INSIGHT HIGH TECH JIANGSU CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The preparation method can overcome the problems of low yield, high cost and difficult industrial implementation in the existing methods, and is a preparation method with low production cost, simple operation and industrial production value

Method used

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  • Preparation method of 3-[(1-(1S)-phenylethyl) amino]-2,3,4,5-tetrahydro-2-oxo-1H-(3S)-benzazepine
  • Preparation method of 3-[(1-(1S)-phenylethyl) amino]-2,3,4,5-tetrahydro-2-oxo-1H-(3S)-benzazepine
  • Preparation method of 3-[(1-(1S)-phenylethyl) amino]-2,3,4,5-tetrahydro-2-oxo-1H-(3S)-benzazepine

Examples

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Embodiment 1

[0018] Example 1: 3-[(1-(1S)-phenethyl)amino]-2,3,4,5-tetrahydro-2-oxo-1H-(3S)-benzazepine (formula I) Preparation

[0019] In a 1000ml reaction flask, add 240.1g (1.0mol) of 3-bromobenzocaprolactam, 54g (0.51mol) of anhydrous sodium carbonate, 127g (1.04mol) of (S)-α-phenylethylamine, and 200ml of ethylene glycol, Stir and heat, keep the reaction at 130-135°C for 7 hours, stop the reaction, cool down to 40°C, add 100ml of ethanol and 300ml of water, stir and cool down, solid precipitates, filter with suction to obtain off-white solid powder, dry to obtain 260g, content: formula 58.4% of compound I, 40.9% of compound of formula III.

[0020] Add 260g of off-white solid powder obtained in the previous step into the reaction flask, and stir in an oil bath at 135°C; react for 40 hours, stop heating, and when the temperature reaches 50°C, add 200g of dichloroethane, heat and stir until dissolved, and cool down to - Keep at 10°C for 2 hours, filter with suction, the filter cake i...

Embodiment 2

[0021] Example 2: 3-[(1-(1S)-phenethyl)amino]-2,3,4,5-tetrahydro-2-oxo-1H-(3S)-benzazepine (formula I) Preparation

[0022] In a 1000ml reaction flask, add 240.1g (1.0mol) of 3-bromobenzocaprolactam, 54g (0.51mol) of anhydrous sodium carbonate, 127g (1.04mol) of (S)-α-phenylethylamine, and 200ml of ethylene glycol, Stir and heat, keep the reaction at 130-135°C for 7 hours, stop the reaction, cool down to 40°C, add 100ml of ethanol and 300ml of water, stir and cool down, solid precipitates, filter with suction to obtain off-white solid powder, dry to obtain 260g, content: formula 58.4% of compound I, 40.9% of compound of formula III.

[0023] Add 260g of off-white solid powder obtained in the previous step into a reaction flask and stir in an oil bath at 160°C; react for 28 hours, stop heating, and when the temperature reaches 80°C, add 140g of toluene, heat and stir until dissolved, cool down, suction filter, filter The cake was white needle-like crystals, 201.7g after dryin...

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Abstract

The invention relates to a preparation method of a key intermediate of a medicine benazepril hydrochloride, that is, 3-[(1-(1S)-phenylethyl) amino]-2,3,4,5-tetrahydro-2-oxo-1H-(3S)-benzazepine. 3-bromo benzo caprolactam and (S)-1-phenylethylamine are used as raw materials; an object product is obtained by amination and a solvent-free configuration transformation reaction; the preparation method has low production cost and simple operations, and has industrial production value.

Description

field of invention [0001] The present invention relates to a preparation method of a compound, in particular to a key intermediate of medicine benazepril hydrochloride namely 3-[(1-(1S)-phenethyl)amino]-2,3,4,5- Preparation method of tetrahydro-2-oxo-1H-(3S)-benzazepine (formula I). Background technique [0002] Benazepril hydrochloride, chemical name: 3-{[1-ethoxycarbonyl-3-phenyl-(1S)-propyl]amino}2,3,4,5-tetrahydro-2-oxo- 1H-1-(3S)-Benzazepine-1-acetic acid hydrochloride (Formula II). Benazepril hydrochloride is a highly active angiotensin-converting enzyme inhibitor, which can reduce peripheral vascular resistance, but will not cause compensatory fluid retention; can reduce afterload, but does not produce counter-regulation; can improve high blood pressure Glucose tolerance of blood pressure diabetics can effectively treat moderate to mild hypertension. [0003] [0004] 3-[(1-(1S)-phenethyl)amino]-2,3,4,5-tetrahydro-2-oxo-1H-(3S)-benzazepine The key intermediate ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D223/16
Inventor 赵文超杜西莹闫庆金罗必奎王永林邵俊峰方玉丽
Owner INSIGHT HIGH TECH JIANGSU CO LTD
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