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Method for preparing vilazodone intermediate 5-piperazinyl-2-acyl substituted benzofuran

A technology of acyl substitution and benzofuran, which is applied in the field of preparation of vilazodone intermediate 5-piperazinyl-2-acyl substituted benzofuran, and can solve the problem of unsubstituted 5-piperazinyl-2-acyl Preparation methods of benzofuran and other issues

Active Publication Date: 2013-12-25
陕西步长高新制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0029] Therefore, there is not yet a relatively perfect preparation method for vilazodone intermediate 5-piperazinyl-2-acyl substituted benzofuran, and it is necessary to continue to explore and screen

Method used

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  • Method for preparing vilazodone intermediate 5-piperazinyl-2-acyl substituted benzofuran
  • Method for preparing vilazodone intermediate 5-piperazinyl-2-acyl substituted benzofuran
  • Method for preparing vilazodone intermediate 5-piperazinyl-2-acyl substituted benzofuran

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Example 1 Add 5-chloro-2-amidobenzofuran (3.91g, 0.02mol), piperazine (3.44g, 0.04mol), copper chloride (0.27g, 0.002mol) into a 100ml three-necked flask, and dimethylsulfoxide (50ml), heated and stirred at 150°C for reaction. The reaction was monitored by thin-layer chromatography. After the reaction was completed, the solvent was removed, and 10 ml of ether was added to the system, and stirred vigorously, and a solid precipitated out. The solid was recrystallized in ethyl acetate to obtain 3.52 g of 5-piperazinyl-2-amidobenzofuran with a yield of 72%.

[0044] MS (ESI + , m / e): 246.12 [M+H] +

[0045] 1 H-NMR (400MHz, CDCl 3 )δ(ppm):1.91(m,1H),2.78(m,4H),3.46(m,4H),6.52(s,1H),7.78(s,1H),7.48(s,1H),7.59( s,1H),7.85(s,2H)

Embodiment 2

[0046] Example 2 Add 5-chloro-2-amidobenzofuran (3.91g, 0.02mol), piperazine (4.30g, 0.05mol), copper bromide (0.45g, 0.002mol) into a 100ml three-necked flask, and dichloromethane (50ml), heated and stirred at 150°C for reaction. The reaction was monitored by thin-layer chromatography. After the reaction was completed, the solvent was removed, and 10 ml of ether was added to the system, and stirred vigorously, and a solid precipitated out. The solid was recrystallized in ethyl acetate to obtain 3.33 g of 5-piperazinyl-2-amidobenzofuran with a yield of 68%.

Embodiment 3

[0047] Example 3 Add 5-bromo-2-amidobenzofuran (4.80g, 0.02mol), piperazine (5.16g, 0.06mol), copper cyanide (0.23g, 0.002mol) into a 100ml three-necked flask, and dimethylformamide (50ml), heated and stirred at 150°C for reaction. The reaction was monitored by thin-layer chromatography. After the reaction was completed, the solvent was removed, and 10 ml of ether was added to the system, and stirred vigorously, and a solid precipitated out. The solid was recrystallized from ethyl acetate to obtain 3.43 g of 5-piperazinyl-2-amidobenzofuran with a yield of 70%.

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Abstract

The invention discloses a method for preparing a vilazodone intermediate 5-piperazinyl-2-acyl substituted benzofuran. By the method, a corresponding vilazodone intermediate 5-piperazinyl-2-acyl substituted benzofuran is obtained by performing a coupling reaction on 5-halogen-substituted-2-acyl substituted benzofuran and piperazine under the actions of copper serving as a catalyst and a suitable solvent. The invention provides a new method for preparing the vilazodone intermediate 5-piperazinyl-2-acyl substituted benzofuran, has the advantages of short course, conveniences in synthesis, high yield, low cost and the like, and is suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of vilazodone intermediate 5-piperazinyl-2-acyl substituted benzofuran. Background technique [0002] Vilazodone hydrochloride, the chemical name is 5-(4-(4-(5-cyano-3-indolyl)butyl)-1-piperazinyl)benzofuran-2-methyl Amide hydrochloride is a new antidepressant drug developed by Clinical Data. In January 2011, it was approved by the US Food and Drug Administration (FDA) for the treatment of depression in adults. Its chemical structure is as follows: [0003] [0004] Vilazodone hydrochloride is a new type of antidepressant with dual effects of 5-HT1A receptor partial agonism and 5-HT reuptake inhibition. Compared with existing clinical antidepressants, it has a rapid onset of action and no side effects of sexual dysfunction for patients Features. [0005] At present, domestic and foreign literatures have disclosed and adopted the following methods to prepare vilazodone hydrochloride: [0006] 1) A pr...

Claims

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Application Information

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IPC IPC(8): C07D307/85
Inventor 赵步长赵超
Owner 陕西步长高新制药有限公司
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