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The synthetic method of vilazodone and its salt

A synthesis method and vilazodone technology are applied in the field of drug synthesis, can solve the problems of being unsuitable for large-scale industrial production of vilazodone hydrochloride, reduce the utilization rate of production resources, increase the cost of equipment use, etc., and achieve simple post-reaction treatment. Easy operation, low price, and the effect of improving product yield

Active Publication Date: 2016-03-09
SUZHOU UUGENE BIOPHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this route uses highly toxic and expensive sodium cyanoborohydride as a selective reducing agent, and the intermediate 3-(4-chlorobutyl)-5-cyanindole is synthesized by oxidation, which requires column chromatography Purification, long reaction time, reducing the utilization rate of production resources, and increasing the use cost of equipment, so this synthetic method is only suitable for small-scale experiments, and is not suitable for large-scale industrial production of vilazodone hydrochloride

Method used

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  • The synthetic method of vilazodone and its salt
  • The synthetic method of vilazodone and its salt
  • The synthetic method of vilazodone and its salt

Examples

Experimental program
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Embodiment 1

[0049] At room temperature, under nitrogen protection, 2.4g of 1.1-dimethoxy-6-chlorohexane was dissolved in a mixed solution of 24mL of ethanol and 12mL of water, and the temperature was raised to 68°C to completely dissolve. At room temperature, a mixed solvent of 1.9g of 4-cyanophenylhydrazine hydrochloride, 19mL of ethanol and 9.5mL of pure water was slowly added dropwise to the 2.3g of 1.1-dimethoxy-6-chlorohexane reaction solution. Keep warm at 70°C for 0.8 hours, wait for the reaction solution to cool down to room temperature, a large amount of solid precipitates, filter with suction, and recrystallize the filter cake with 50% ethanol aqueous solution to obtain 1.98g of 3-(4-chlorobutyl)-5-cyanoindol Indole.

[0050] Under the protection of nitrogen, dissolve 4.0g of 5-fluoro-2-hydroxybenzaldehyde in 15mL of acetonitrile to form a reaction solution, add 3.26g of cesium carbonate to the reaction solution under stirring, stir for 10 minutes under the protection of nitroge...

Embodiment 2

[0055] At room temperature, under nitrogen protection, 6.5g of 1.1-dimethoxy-6-chlorohexane was dissolved in a mixed solution of 65mL of methanol and 35mL of water, and the temperature was raised to 70°C to completely dissolve. At room temperature, a mixed solvent of 6.0g of 4-cyanophenylhydrazine hydrochloride, 60mL of methanol and 30mL of pure water was slowly added dropwise to the 5.9g of 1.1-dimethoxy-6-chlorohexane reaction solution, at 72 Keep warm at ℃ for 1.0 hour, wait for the reaction liquid to drop to room temperature, a large amount of solid precipitates, filter with suction, and recrystallize the filter cake with 53% ethanol aqueous solution to obtain 8.0 g of 3-(4-chlorobutyl)-5-cyanindole .

[0056]Under the protection of nitrogen, dissolve 7.0g of 5-fluoro-2-hydroxybenzaldehyde in 70mL of N,N-dimethylformamide to form a reaction solution, add 3.0g of triethylamine to the reaction solution under stirring, and stir for 9 Minutes later, 4.1 g of bromoacetamide wa...

Embodiment 3

[0061] At room temperature, 4.5g of 1.1-dimethoxy-6-chlorohexane was dissolved in a mixed solution of 45mL of ethanol and 25mL of water under the protection of nitrogen, and the temperature was raised to 72°C to completely dissolve. At room temperature, a mixed solvent of 3.9g of 4-cyanophenylhydrazine hydrochloride, 39mL of ethanol and 10mL of pure water was slowly added dropwise to the reaction solution of 3.9g of 1.1-dimethoxy-6-chlorohexane, at 72 Keep warm at ℃ for 1.1 hours, wait for the reaction liquid to drop to room temperature, a large amount of solids precipitate out, filter with suction, and recrystallize the filter cake with 55% ethanol aqueous solution to obtain 6.0 g of 3-(4-chlorobutyl)-5-cyanindole .

[0062] Under the protection of nitrogen, dissolve 4.5g of 5-fluoro-2-hydroxybenzaldehyde in 45mL of tetrahydrofuran to form a reaction solution, add 3.9g of N-methylmorpholine to the reaction solution under stirring, stir for 11 minutes under the protection of n...

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Abstract

The invention relates to a synthesis method of vilazodone and a salt thereof, belonging to the technical field of drug synthesis. The synthesis method comprises the following steps of: with 5-fluorin-2-hydroxybenzaldehyde as a raw material, subjecting the 5-fluorin-2-hydroxybenzaldehyde and acetobromamide to reaction under the action of an acid binding agent to obtain a compound as shown in the formula (I); subjecting piperazine and the compound (I) as shown in the formula (I) to reaction at the temperature of 100-140 DEG C under the action of alkaline to obtain a compound as shown in the formula (II); and subjecting 3-(4-chlorobutyl)-5-cyanoindole and the compound as shown in the formula (II) to reflux reaction for 14-18h under the actions of a catalyst and alkaline, and then, adding the product into an aqueous alkaline solution until a solid is separated out to obtain a compound as shown in the formula (III), namely the vilazodone, wherein the compounds as shown in the formulas (I), (II) and (III) respectively have the structural formulas in the specification. The synthesis method is low in production cost, environment-friendly, high in conversion ratio, few in byproducts, high in product yield and purity, good in quality and suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to a synthesis method of vilazodone and a salt thereof, belonging to the technical field of medicine synthesis. Background technique [0002] The chemical name of Vilazodone is 5-(4-(4-(5-cyano-3-indolyl)butyl)-1-piperazinyl)benzofuran-2-carboxamide, and its English name is 5 -(4-(4-(5-Cyanoindol-3-yl)butyl)-1-piperazinyl)-2-benzofurancarboxamide, the chemical structural formula is: [0003] [0004] The chemical structural formula of vilazodone salt is: [0005] Among them, HX is obtained from hydrochloric acid, sulfuric acid, hydrobromic acid, acetic acid, tartaric acid, maleic acid, fumaric acid, oxalic acid, citric acid, phosphoric acid, trifluoroacetic acid, formic acid, succinic acid, mandelic acid, methanesulfonic acid, p-toluene One of sulfonic acid, benzoic acid, p-nitrobenzoic acid, and p-hydroxybenzoic acid. [0006] Vilazodone and its salts are new antidepressant drugs developed by ClinicalData for the treatmen...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/12
Inventor 胡凡王伸勇邵长坤李胜王晓俊胡长春
Owner SUZHOU UUGENE BIOPHARMA
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