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Preparation method of dapoxetine

A technology of dapoxetine and reaction time, which is applied in the field of preparation of the compound dapoxetine, can solve the problems of unsatisfactory large-scale industrial production, harsh reaction conditions, low yield, etc., to overcome harsh reaction conditions and simple operation , good yield effect

Inactive Publication Date: 2012-10-24
湖南尔文水电建材有限公司
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  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0020] There are harsh reaction conditions and low yields in the above methods, which cannot meet the requirements of large-scale industrial production.

Method used

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  • Preparation method of dapoxetine
  • Preparation method of dapoxetine
  • Preparation method of dapoxetine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Dissolve 12g of acetophenone in 100mL of acetonitrile, add 10g of triethylamine, 19g of sodium iodide, and 10g of magnesium chloride in sequence, the reaction temperature is 25°C, and the reaction time is 4 hours. After the reaction, add dilute sodium hydroxide aqueous solution, then add ethyl acetate, extract and separate, collect the aqueous phase, then add dilute hydrochloric acid, then add ethyl acetate, extract and separate, collect the organic phase, dry and concentrate to obtain 15.8 gCompound 2.

[0045] IR (KBr) (cm -1 ): 3328, 3215, 2850, 1740, 1600, 1430, 750,700.

Embodiment 2

[0047] Mix 15g of 2 with 200mL of methanol, add 24g of thionyl chloride, the reaction temperature is 80°C, and the reaction time is 1 hour. After the reaction was completed, methanol and thionyl chloride were removed under reduced pressure to obtain 15.8 g of compound 3.

[0048] IR (KBr) (cm -1 ): 3327, 3214, 2960, 2849, 1980, 1739, 1599, 1428, 749,698.

Embodiment 3

[0050] Dissolve 15g of 3 in 100mL of ethanol, add 5.9g of hydroxylamine hydrochloride and 80mL of 0.1M NaOH aqueous solution, the reaction temperature is 25°C, and the reaction time is 2 hours. After the reaction was completed, ethanol was removed under reduced pressure, water and ethyl acetate were added for extraction and separation, and the organic phase was collected, dried, and concentrated to obtain 13.6 g of compound 4.

[0051] IR (KBr) (cm -1 ): 3325, 3300, 3212, 2959, 2848, 1979, 1738, 1598, 1426, 747, 697.

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Abstract

The invention provides a preparation method of dapoxetine, which comprises the following steps: based on acetophenone as a starting raw material, and carrying out carboxylation, esterification, hydroxy imine formation, reduction, Boc protection, condensation, methylation and resolution to prepare dapoxetine. The method has the advantages that the synthesis process is green and environment-friendly, toxic and harmful reagents are not used, the discharge of three wastes is reduced, the operation is easy and simple, the yield is greatly improved, and industrial production is favorably realized.

Description

technical field [0001] The invention relates to a preparation method of chemical medicine, in particular to a preparation method of the compound dapoxetine. Background technique [0002] Dapoxetine, English name Dapoxetine, chemical name (S-(+)-N,N-Dimethyl-a -[2-(naphthalenyloxy)ethyl]benzonemethanamine, CAS: 119356-77-3, structural formula: [0003] [0004] Dapoxetine (dapoxetine), as a new type of rapid SSRI, has a short half-life and is a selective serotonin reuptake inhibitor (SSRI). It was developed by Eli Lilly and was launched in Europe in 2009. The trade name is Priligy, which is used to treat premature ejaculation in men. The drug has a short half-life, few adverse reactions, and significant effects. It is the first oral prescription drug approved for the treatment of PE in the world. [0005] At present, the disclosed synthetic methods of dapoxetine are as follows: [0006] 1. W. J and P.D.B Abstracts [0007] synthetic route: [0008] 1) [0009] ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C217/48C07C213/08
Inventor 陈芳军
Owner 湖南尔文水电建材有限公司
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