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Method for preparing 1-[2-(2,5-dimethylphenylthio)phenyl]piperazine

A technology of dimethylphenylthio and dimethylthiophenol, which is applied in the field of chemical substance preparation, can solve problems such as the safety impact of vortioxetine hydrobromide, achieve high yield, short synthetic route, and selective sex high effect

Inactive Publication Date: 2018-05-11
安徽源久源科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, there are multiple synthetic routes for preparing vortioxetine hydrobromide, but a series of impurities will be produced in the preparation process, and the existence of impurities will affect the drug safety of vortioxetine hydrobromide, so it is necessary to Impurities are monitored to ensure the safety and effectiveness of drugs

Method used

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  • Method for preparing 1-[2-(2,5-dimethylphenylthio)phenyl]piperazine
  • Method for preparing 1-[2-(2,5-dimethylphenylthio)phenyl]piperazine

Examples

Experimental program
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Effect test

Embodiment 1

[0034] A preparation method of 1-[2-(2,5-dimethylphenylthio)phenyl]piperazine, comprising the steps of:

[0035] S1. In an inert gas atmosphere, mix 1,1'-binaphthyl-2,2'-bisdiphenylphosphine, sodium tert-butoxide, toluene, bis(dibenzylideneacetone)palladium, and stir at room temperature for 12 minutes. Solution A was added dropwise, then refluxed for 14 hours, cooled to room temperature, and the filtrate was filtered, wherein the solute of solution A was 2,5-dimethylthiophenol and o-iodobromobenzene, and the solvent was toluene;

[0036] S2. Add 1,1'-binaphthyl-2,2'-bisdiphenylphosphine, sodium tert-butoxide, bis(dibenzylideneacetone) palladium and piperazine to the filtrate obtained in S1, and in an inert gas atmosphere , refluxed for 4 hours, cooled to room temperature, mixed with water, and purified to obtain 1-[2-(2,5-dimethylphenylthio)phenyl]piperazine.

Embodiment 2

[0038] A preparation method of 1-[2-(2,5-dimethylphenylthio)phenyl]piperazine, comprising the steps of:

[0039] S1. In a nitrogen atmosphere, mix 1,1'-binaphthyl-2,2'-bisdiphenylphosphine, sodium tert-butoxide, toluene, bis(dibenzylideneacetone)palladium, stir at room temperature for 10 minutes, drop Add solution A, then reflux for 16h, cool to room temperature, and filter to get the filtrate, wherein the solute of solution A is 2,5-dimethylthiophenol and o-iodobromobenzene, 2,5-dimethylthiophenol The concentration is 0.08g / ml, the concentration of o-iodobromobenzene is 0.23g / ml, and the solvent is toluene, among which, 1,1'-binaphthyl-2,2'-bisdiphenylphosphine, sodium tert-butoxide, bis( The weight ratio of dibenzylideneacetone) palladium is 0.07:4.2:0.033, the weight volume (g / ml) ratio of sodium tert-butoxide to toluene is 2.1:11, 2,5-dimethylthiophenol and tert-butyl The weight ratio of sodium alkoxide is 1:2.1;

[0040] S2. Add 1,1'-binaphthyl-2,2'-bisdiphenylphosphine...

Embodiment 3

[0043] A preparation method of 1-[2-(2,5-dimethylphenylthio)phenyl]piperazine, comprising the steps of:

[0044] S1. In a nitrogen atmosphere, mix 1,1'-binaphthyl-2,2'-bisdiphenylphosphine, sodium tert-butoxide, toluene, bis(dibenzylideneacetone)palladium, stir at room temperature for 15 minutes, drop Add solution A, then reflux for 12h, cool to room temperature, filter and get the filtrate, wherein, the solute of solution A is 2,5-dimethylthiophenol and o-iodobromobenzene, 2,5-dimethylthiophenol The concentration is 0.12g / ml, the concentration of o-iodobromobenzene is 0.19g / ml, and the solvent is toluene, among which, 1,1'-binaphthyl-2,2'-bisdiphenylphosphine, sodium tert-butoxide, bis( The weight ratio of dibenzylideneacetone) palladium is 0.075:4.15:0.0335, the weight volume (g / ml) ratio of sodium tert-butoxide to toluene is 4.15:25, 2,5-dimethylthiophenol and tert-butyl The weight ratio of sodium alkoxide is 2:4.15;

[0045]S2. Add 1,1'-binaphthyl-2,2'-bisdiphenylphosphi...

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Abstract

The invention discloses a method for preparing 1-[2-(2,5-dimethylphenylthio)phenyl]piperazine. The method comprises the following steps: S1, in an inert gas atmosphere, 1,1'-binaphthyl 2,2'-bis(diphenylphosphine), sodium tert-butoxide, toluene, bis (dibenzylideneacetone) palladium are evenly mixed and stirred at room temperature for 10-15 minutes, a solution A is added dropwise, reflux is performed for 12-16 hours, the temperature is reduced to room temperature, and a filtrate is obtained by filtering, wherein a solute of the solution A is 2,5-dimethylthiophenol and o-iodobromobenzene, and a solvent is toluene; S2, 1,1'-binaphthyl-2,2'-bis(diphenylphosphine), sodium tert-butoxide, bis(dibenzylideneacetone)palladium and piperazine are added to the filtrate obtained in S1, the mixed solutionis subjected to reflux for 3-5 h in an inert gas atmosphere and cooled to the room temperature, water is added for uniform mixing, a product is purified, and 1-[2-(2,5-dimethylphenylthio)phenyl]piperazine is obtained.

Description

technical field [0001] The invention relates to the technical field of chemical substance preparation, in particular to a preparation method of 1-[2-(2,5-dimethylphenylthio)phenyl]piperazine. Background technique [0002] Vortioxetine hydrobromide is a new type of bisarylsulfanylamine antidepressant jointly developed by Japan's Takeda and Denmark's Lundbeck. It is used for the treatment of depression and anxiety. In September 2013, it was approved by the United States. The FDA approved the marketing, trade name Brintellix, for the treatment of severe depression in adults. In October of the same year, the Marketing Authorization Application (MAA) of Vortioxetine was approved by the Human Medicinal Products Committee (CHMP) of the European Medicines Agency (EMA). Positive opinion, CHMP recommended to approve Brintellix for the treatment of adult patients with major depressive disorder (MDD). In December 2013, EMA European Commission granted Vortioxetine the right to sell in th...

Claims

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Application Information

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IPC IPC(8): C07D295/096
CPCC07D295/096
Inventor 王贤诗
Owner 安徽源久源科技有限公司
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