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1-[2-(2,4-dimethylphenylsulfydryl)phenyl]piperazine hydrochloride and preparation method thereof

A technology of dimethyl phenyl thiol and xetine hydrochloride, applied in the field of medicine, can solve the problems of many by-products, high price, and the synthesis method is unfavorable for cost control and enlarged production, and achieves simple synthesis process and low cost. Effect

Inactive Publication Date: 2018-04-17
FUKANGREN BIO PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Regardless of the method, a metal palladium complex catalyst is used, which is expensive, and there are many by-products, which are difficult to control, and the synthesis method is not conducive to cost control and enlarged production.

Method used

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  • 1-[2-(2,4-dimethylphenylsulfydryl)phenyl]piperazine hydrochloride and preparation method thereof
  • 1-[2-(2,4-dimethylphenylsulfydryl)phenyl]piperazine hydrochloride and preparation method thereof
  • 1-[2-(2,4-dimethylphenylsulfydryl)phenyl]piperazine hydrochloride and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0021] Add 66.3g of o-fluoronitrobenzene and 65 2,4-dimethylthiophenol into 400mL of N,N-dimethylformamide, add 30g of powdered potassium carbonate under room temperature stirring, and stir at 80°C for 5 hour, after cooling down, a small amount of water was added, and concentrated under reduced pressure; the residue was crystallized with ethyl acetate / petroleum ether mixed solvent to obtain 105 g of a dark yellow solid;

Embodiment 2

[0023] Take 100 g of 2-(2,4-dimethylphenylthio)nitrobenzene obtained in Example 1, add it to 2 L of water, add a catalytic amount of ammonium chloride, and 50 g of iron powder, and heat up to 80° C. for 3 hours. Cool down, filter iron powder, transfer the filtrate to 30% potassium carbonate aqueous solution, after stirring, add ethyl acetate for extraction, and concentrate the organic phase to obtain 73g of 2-(2,4-dimethylphenylthio)aniline;

Embodiment 3

[0025] Add 70g of 2-(2,4-dimethylphenylthio)aniline and 55g of bis(2-chloroethyl)amine hydrochloride to 500mL of toluene, heat to reflux for 36 hours, cool, add 800mL of water and 500mL of Ethyl acetate, liquid separation, the organic phase was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, dilute hydrochloric acid was added dropwise to the filtrate to adjust the pH to 2, stirred, and a solid was precipitated. After filtering, the filter cake was washed with ethyl acetate and dried to obtain 43 g of hydrochloric acid.

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Abstract

The invention discloses 1-[2-(2,4-dimethylphenylsulfydryl)phenyl]piperazine hydrochloride and a preparation method thereof. By means of the specific preparation method, the HPLC purity of vortioxetinehydrochloride is higher than 99.5%, and the content of single impurities is smaller than 0.1%. The invention aims to provide a synthesis process of a compound vortioxetine and vortioxetine hydrochloride, which is high in yield, low in cost and suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to vortioxetine salt and a preparation and purification method thereof, belonging to the technical field of medicine. Background technique [0002] Patent CN1319958C discloses compound vortioxetine (Vortioxetine), its structure is shown in the following formula, and its chemical name is 1-[2-(2,4-dimethylphenylmercapto) phenyl] piperazine, which is produced by Lingbei (Lindbeck) and Takeda (Takeda) jointly developed a 5-hydroxytryptamine transporter inhibitor, its hydrobromide salt was approved by the FDA in September 2013, and the trade name is Brintellix, which is clinically used for the treatment of toxic depression and generalized anxiety disorder . [0003] [0004] Patent CN101472906B first discloses the forms of vortioxetine hydrobromide, hydrochloride, mesylate, and maleate, and their synthesis methods. Method 1: 2-bromo-iodobenzene, 2,4-dimethylthiophenol, Boc-piperazine in toluene solvent, under the catalysis of pal...

Claims

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Application Information

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IPC IPC(8): C07D295/096
CPCC07D295/096
Inventor 张俊
Owner FUKANGREN BIO PHARMA
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