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Preparation method of diaryl sulfide amine compounds

A technology of dimethylphenylsulfanyl and phenyl, which is applied in the field of preparation of 1-[2-phenyl]piperazine derivatives, can solve problems such as difficult purification and coupling impurities, and achieve high sample purity , low cost and high yield

Active Publication Date: 2020-03-03
JIANGSU HANSOH PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The patent protects the above route from many factors such as solvent, alkali and palladium source used; at the same time, the patented synthesis method will lead to the generation of other coupling impurities during the reaction process, which will bring difficulties to subsequent purification

Method used

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  • Preparation method of diaryl sulfide amine compounds
  • Preparation method of diaryl sulfide amine compounds
  • Preparation method of diaryl sulfide amine compounds

Examples

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Embodiment 1

[0060]Example 1: Synthesis of 2-{4-[2-(2,4-dimethylphenylsulfanyl) phenyl] piperazin-1-yl} ethyl acetate

[0061]

[0062] Add 28.5g (0.16mol) of bis(2-chloroethyl)amine hydrochloride and 200ml of ethanol to a 500ml three-necked flask, heat up to 80°C, stir for 1 hour, and add 21.7g (0.17mol) of 2-chloroaniline , anhydrous sodium carbonate 7.4g (0.07mol), continue to heat and stir the reaction for 25h, cool to room temperature, filter with suction, the filtrate is concentrated to dryness, add acetonitrile 100ml for crystallization, and obtain 35.8g of white crystals, the yield is 96%.

[0063] Dissolve 14.0g (0.06mol) of 1-(2-chlorophenyl)piperazine hydrochloride in 100ml of anhydrous methanol, add dropwise saturated sodium bicarbonate solution to adjust the pH to 8-9 while stirring, cool, and filter with suction. The filtrate was concentrated to dryness to obtain a white solid, namely 1-(2-chlorophenyl)piperazine.

[0064] Dissolve the above solid in 100ml N,N-dimethylfor...

Embodiment 2

[0066] Embodiment 2: the synthesis of 1-[2-(2,4-dimethylphenylsulfanyl) phenyl] piperazine hydrobromide

[0067]

[0068] Add 28.5g (0.16mol) of bis(2-chloroethyl)amine hydrochloride and 200mL of butanol into a 500ml three-necked flask, heat up to 80°C, stir for 1h, add 29.2g (0.17mol) of 2-bromoaniline ) and anhydrous potassium carbonate 9.7g (0.07mol), continue to insulate and stir the reaction for 25h, cool to room temperature, filter with suction, concentrate the filtrate to dryness, add 100ml of acetonitrile for crystallization, and obtain 42.2g of white crystals with a yield of 95%.

[0069] Dissolve 16.6g (0.06mol) of 1-(2-bromophenyl)piperazine hydrochloride in 100ml of absolute ethanol, add a saturated sodium bicarbonate solution dropwise under stirring to adjust the pH to 8-9, cool, and filter with suction. The filtrate was concentrated to dryness to obtain a solid which was 1-(2-bromophenyl)piperazine.

[0070] Dissolve the above solid in 100ml of absolute ethan...

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Abstract

The invention relates to a preparation method for a diaryl thioether amine compound. Specifically, the invention relates to a preparation method for 1-[2-(2,4-dimethylphenylsulfalkyl)phenyl]piperazine derivative as shown in a formula I which is described in the specification. The preparation method comprises the following steps: subjecting a compound as shown in a formula V and a compound as shown in a formula IV to cyclization, condensation or introduction of an amino protective group; carrying out further condensation; etc. Thus, the target compound is obtained. Compared with other methods, the preparation method provided by the invention has the advantages of good process reproducibility and easy operation and the characteristics of high yield, low cost and high product purity, is more suitable for industrial production and has higher economic benefits.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of 1-[2-(2,4-dimethylphenylsulfanyl)phenyl]piperazine derivatives with high purity and suitable for industrial production. Background technique [0002] 1-[2-(2,4-Dimethylphenylsulfanyl)phenyl]piperazines are diarylsulfide amines. In September 2013, the compound 1-[2-(2,4-dimethylphenylsulfanyl)phenyl]piperazine hydrobromide, approved by the FDA, is a new chemical class of antidepressants. Mainly used to treat depression and anxiety. This product was jointly developed by Lundbeck and Takeda. In the patent CN102617513A, the preparation method of this compound was specifically protected. The key points of the protection are as follows: [0003] [0004] The overall idea of ​​the above-mentioned protection can basically be summarized into the following two types: [0005] [0006] The patent protects the above-mentioned route from ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D295/15C07D295/096
CPCC07D295/096C07D295/15Y02P20/55
Inventor 曹金游军辉杜祖银赵军军戚郜飞
Owner JIANGSU HANSOH PHARMA CO LTD
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