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Method for preparing vilazodone

A technology of vilazodone and formate, which is applied in the field of preparation of antidepressant vilazodone, can solve the problems of harmful organic transition metal catalysts and expensive environment

Inactive Publication Date: 2014-01-22
SHANGHAI AOBO PHARMTECH INC LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] The disadvantage of this synthetic route is the need to use expensive and environmentally harmful organotransition metal catalysts

Method used

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  • Method for preparing vilazodone
  • Method for preparing vilazodone
  • Method for preparing vilazodone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] 150 grams of 5-nitrosalicylaldehyde are added to the reaction flask, then 300 grams of potassium bicarbonate and 1000 milliliters of ethanol are added, and stirred evenly; 236 grams of diethyl bromomalonate are added, heated and refluxed overnight; TLC tracks to The reaction was basically completed, cooled to room temperature, filtered, the filter cake was washed with 900 mL of water, and the filter cake was taken out and dried to obtain 139 grams of 5-nitrophenylpropane-2-carboxylate (III), with a yield of 66% and a purity of 99.3 %.

Embodiment 2

[0036] The preparation of embodiment two 5-aminobenzofuran-2-ethyl carboxylate (IV)

[0037] 100 grams of 5-nitrobenzofuran-2-carboxylate (III), 10 grams of 7% palladium / carbon, and 800 milliliters of ethanol were successively added to the reaction flask, and after hydrogen replacement for 3 times, they were stirred at room temperature and tracked by TLC. until the reaction is complete. After filtration, the filtrate was concentrated directly to obtain 85 g of ethyl 5-aminobenzofuran-2-carboxylate (IV) as an oil, which was directly used in the next reaction. The preparation of embodiment three 5-piperazinyl benzofuran-2-ethyl carboxylate (V)

Embodiment 3

[0038] 119 grams of ethyl 5-aminobenzofuran-2-carboxylate (IV) is added in the reaction flask, 260 grams of two (2-chloroethylamine) hydrochloride and 2500 milliliters of ethanol are added, then 160 grams of potassium carbonate are added ; Protected after nitrogen replacement, heated to reflux overnight. HPLC traces the reaction until the remaining ≤ 7% of the raw material is the end point of the reaction; the reaction solution is cooled to room temperature, filtered, the filter cake is washed with water, and the filter cake is taken out and dried to obtain 80 grams of off-white solid 5-piperazinylphenylpropane-2-carboxylic acid Ethyl ester (V), yield 50%, purity 98.5%. The preparation of embodiment four 5-piperazinyl benzofuran-2-carboxamide (VI)

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Abstract

The invention discloses a method for preparing an antidepressant medicine vilazodone (I). The method comprises the steps of (1) enabling 5-nitrosalicylaldehyde (II) to react with 2-bromomalonic acid diester under an alkali effect to generate 5-nitrobenzopropylfurazan-2-formate (III); then generating 5-aminobenzopropylfuran-2-formate (IV) under the effect of a reducing agent from the (III); enabling the (IV) to react with bi(2-chloroethyl)amine to generate 5-piperazinobenzopropylfuran-2-formate (V); enabling the obtained (V) to react with ammonia gas or an ammonia gas solution to generate 5-piperazinobenzopropylfuran-2-formamide (VI); finally, performing a coupling reaction between the (VI) and 3-(4-chlorobutyl)-5-cyanoindole under an alkaline condition to obtain the vilazodone (I).

Description

technical field [0001] The present invention relates to the preparation method of antidepressant vilazodone (vilazodone) (I). Background technique [0002] Depression is a disease caused by changes in brain biochemistry, and its clinical manifestations are low mood, pessimism, and sleep disturbance. Low levels of monoamine neurotransmitters such as 5-hydroxytryptamine (5-HT), dopamine, and low receptor function are considered to be the cause of depression. The latest drug for the treatment of depression is selective 5-HT reuptake inhibitor (SSRI), which can inhibit the reuptake of 5-HT in the presynaptic membrane, increase the concentration of 5-HT in the synaptic cleft, and improve the Postsynaptic 5-HT 1A Excitability of receptors, resulting in antidepressant effects. In addition, it does not affect other neurotransmitter receptors, so it is relatively safe. 5-HT 1A The receptor is 5-HT 1 One of the members of the receptor family, which is further divided into presyn...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/12C07D307/85
CPCC07D405/12C07D307/85
Inventor 竺伟袁利陈欢生陈宇
Owner SHANGHAI AOBO PHARMTECH INC LTD
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