Preparation method of Naftopidil

A technology of naftopidil and naphthyloxy, which is applied in the field of preparation of naftopidil, can solve the problems of high energy consumption, poor color, low yield, etc., and achieve the effect of improving yield

Active Publication Date: 2011-04-27
蚌埠丰原涂山制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] The purpose of this invention is to provide a kind of preparation method of naftopidil, to solve the low yield in the original technology, the problem of poor color and large energy consumption

Method used

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  • Preparation method of Naftopidil

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Experimental program
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Effect test

Embodiment 1

[0024] 1) Naftopidil preparation:

[0025] In a 5000ml three-necked bottle, install a thermometer, a condenser, and a mechanical stirrer. Add 3-(1-naphthyloxy)-1,2-propylene oxide 326.3g (content about 77%, 1.26mol), o-methoxyphenylpiperazine hydrobromide 366g (1.26mol), potassium carbonate 95.7 g (0.69 mol) was dissolved in 100 g of purified water and 600 ml of chloroform, and refluxed for 8 hours under stirring. Cool to room temperature, filter, and wash the filter residue with 300ml of chloroform. The filtrate was washed twice with purified water, the organic layer was separated, and concentrated to dryness under reduced pressure to obtain 551 g of a black oil. Add 700ml of absolute ethanol, heat to dissolve, add 15g of activated carbon, continue to heat and reflux for 10 minutes, suction filter while hot, cool to room temperature with stirring, cool in an ice-water bath for 3 hours, precipitate a large amount of crystals, filter with suction, and dry to obtain a yellowis...

Embodiment 2

[0029] In a 5000ml three-necked bottle, install a thermometer, a condenser, and a mechanical stirrer. Add 3-(1-naphthyloxy)-1,2-propylene oxide 300g (content about 77%, 1.15mol), o-methoxyphenylpiperazine hydrobromide 350g (1.20mol), potassium carbonate 90g (0.65mol) was dissolved in 100g of purified water, 600ml of chloroform, and refluxed under stirring for 7 hours. Cool to room temperature, filter, and wash the filter residue with 300ml of chloroform. The filtrate was washed twice with purified water, the organic layer was separated, and concentrated to dryness under reduced pressure to obtain 540 g of a black oil. Add 700ml of absolute ethanol, heat to dissolve, add 15g of activated carbon, continue to heat and reflux for 20 minutes, suction filter while hot, cool to room temperature with stirring, cool in an ice-water bath for 3 hours, precipitate a large amount of crystals, filter with suction, and dry to obtain a yellowish solid 492g, yield 83.6%. mp: 125-127°C, the ...

Embodiment 3

[0033] In a 5000ml three-necked bottle, install a thermometer, a condenser, and a mechanical stirrer. Add 245g of 3-(1-naphthyloxy)-1,2-propylene oxide (content about 77%, 0.94mol), o-methoxyphenylpiperazine hydrobromide 276g (0.95mol), potassium carbonate 76g (0.55mol) was dissolved in 80g of purified water and 480ml of dichloromethane, and refluxed under stirring for 6.0 hours. Cool to room temperature, filter, and wash the filter residue with 250ml of dichloromethane. The filtrate was washed twice with purified water, the organic layer was separated, and concentrated to dryness under reduced pressure to obtain 450 g of a black oil. Add 600ml of absolute ethanol, heat to dissolve, add 15g of activated carbon, continue to heat and reflux for 10 minutes, suction filter while it is hot, cool to room temperature while stirring, and cool in an ice-water bath for 5 hours, a large amount of crystals precipitate, suction filter, and dry to obtain a yellowish solid 402g, yield 83.7...

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Abstract

The invention provides a preparation method of Naftopidil. In the presence of reaction solvent, a reflux reaction is carried out between 3-(1-naphthoxy)-1,2-propylene epoxide and o-methoxyphenyl piperazine hydrobromide, and then refined processing is carried out after the reaction, wherein, the reaction solvent is trichloromethane or dichloromethane; and the alkali matter is potassium carbonate water solution. The method in the invention improves the yield, improves the reaction yield to about 80% from the original 55-65%; and the refined products are white or almost white crystals, and the product quality accords with the medicinal requirement.

Description

technical field [0001] The invention relates to a preparation method of naftopidil. Background technique [0002] Naftopidil chemical name: (±)-1-[4-(2-methoxyphenyl)-1-piperazinyl]-3-(1-naphthyloxy)-2-propanol. Molecular formula: C 24 h 28 N 2 o 3 , molecular weight: 392.50. It is white or off-white crystalline powder. [0003] Naftopidil can reduce the total peripheral resistance and dilate peripheral blood vessels in anesthetized thoracotomy dogs, but has no significant effect on cardiac output. It can also relieve the tension of the sympathetic nerves distributed in the prostate and urethra, reduce the internal pressure of the urethra, and improve dysuria caused by prostatic hypertrophy. High blood pressure, especially suitable for patients with high blood pressure accompanied by hyperlipidemia, diabetes, and benign prostatic hyperplasia. [0004] According to the disclosed 1-[3-(1-naphthyloxy)-2-hydroxypropyl]-piperazine compound and therapeutic components of U....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D295/096
Inventor 张祖扬汪洪湖王劲松吴立军
Owner 蚌埠丰原涂山制药有限公司
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