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New preparation process of sargrel hydrochloride

A technology of sarpogrelate hydrochloride and methoxyphenyl, which is applied in the field of preparation of sarpogrelate hydrochloride, can solve the problems of low reaction yield, inconvenient operation, danger and the like, and achieves simple reaction operation, improved yield and avoided danger. The effect of reagent use

Active Publication Date: 2016-05-25
ANHUI AN TECH MEDICAL & BIOLOGICAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Its synthesis method uses the dangerous reagent sodium hydride, and there are problems such as low reaction yield and inconvenient operation.

Method used

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  • New preparation process of sargrel hydrochloride
  • New preparation process of sargrel hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] 2-[2-(3-methoxyphenyl) ethyl]phenol (22.83g, 0.1mol) was dissolved in toluene (120ml), sodium hydroxide (4.8g, 0.12mol), water (80ml), benzyl Triethylammonium chloride (1.378, 0.006mol), epichlorohydrin (10.97ml, 0.14mol), warming up to reflux for 8 hours, cooling and standing to separate layers, the organic layer was washed with water (80ml×2), and no dried over sodium sulfate, filtered, and the filtrate was concentrated to dryness under reduced pressure to give a light yellow oil [[2-[2-(3-methoxyphenyl)ethyl]phenoxy]methyl]oxirane ( 27.8g, yield 97.8%), directly used in next step reaction.

[0018] Reactor selects laboratory autoclave, [[2-[2-(3-methoxyphenyl) ethyl] phenoxy] methyl] oxirane (27.8g, 0.098mol) is dissolved in tetrahydrofuran (150ml ), add 33% dimethylamine aqueous solution (14.88g, 0.108mol), feed nitrogen into the kettle, pressurize to 0.1MPa, stir and react for 3 hours. The solvent was evaporated under reduced pressure, ethyl acetate (150ml) and w...

Embodiment 2

[0021] 2-[2-(3-Methoxyphenyl) ethyl]phenol (45.66g, 0.2mol) was dissolved in toluene (240ml), sodium hydroxide (9.6g, 0.24mol) was added, water (160ml), Benzyltriethylammonium chloride (2.74g, 0.012mol), epichlorohydrin (21.94ml, 0.28mol), heated to reflux for 8 hours, cooled and stood still to separate layers, and the organic layer was washed with water (160ml×2) , dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to dryness under reduced pressure to give light yellow oil [[2-[2-(3-methoxyphenyl)ethyl]phenoxy]methyl]oxirane Alkane (54.2g, yield 95.3%) was directly used in the next reaction.

[0022] Reactor selects laboratory autoclave, [[2-[2-(3-methoxyphenyl) ethyl] phenoxy] methyl] oxirane (54.2g, 0.191mol) is dissolved in tetrahydrofuran (300ml ), add 33% dimethylamine aqueous solution (28.99g, 0.210mol), feed nitrogen into the kettle, pressurize to 0.1MPa, stir and react for 3 hours. The solvent was evaporated under reduced pressure, ethy...

Embodiment 3

[0025] 2-[2-(3-methoxyphenyl) ethyl]phenol (91.32g, 0.4mol) was dissolved in toluene (480ml), sodium hydroxide (19.2g, 0.48mol) was added, water (320ml), Benzyltriethylammonium chloride (5.48g, 0.024mol), epichlorohydrin (43.88ml, 0.56mol), warming up to reflux for 8 hours, cooling and standing to separate layers, the organic layer was washed with water (320ml×2) , dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to dryness under reduced pressure to give light yellow oil [[2-[2-(3-methoxyphenyl)ethyl]phenoxy]methyl]oxirane Alkane (110.8g, yield 97.4%) was directly used in the next reaction.

[0026] Reactor selects laboratory autoclave, [[2-[2-(3-methoxyphenyl) ethyl] phenoxy] methyl] oxirane (110.8g, 0.390mol) is dissolved in tetrahydrofuran (600ml ), add 33% dimethylamine aqueous solution (59.22g, 0.429mol), feed nitrogen into the kettle, pressurize to 0.1MPa, and stir for 3 hours. The solvent was evaporated under reduced pressure, ethyl ace...

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Abstract

The present invention discloses a preparation method of sarpogrelate hydrochloride. According to the preparation method, 2-[2-(3-methoxyphenyl)ethyl]phenol is adopted as a starting reactant, benzyl triethylammonium chloride is adopted as a phase transfer catalyst, the starting reactant, the phase transfer catalyst and epichlorohydrin form an ether in toluene and water, dimethylamine is adopted to carry out aminolysis in a pressurization reactor after the ether is formed to obtain 1-dimethylamino-3-[2-[2-(3-methoxyphenyl)ethyl]phenoxy]-2-propanol, the 1-dimethylamino-3-[2-[2-(3-methoxyphenyl)ethyl]phenoxy]-2-propanol and succinic anhydride are subjected to esterification in acetone, hydrogen chloride gas is directly introduced without recovery and replacement of the solvent to form a hydrochloride, and re-crystallization with acetone is performed to obtain the sarpogrelate hydrochloride refined product, wherein the purity is more than 99%.

Description

1. Technical field [0001] The invention relates to a preparation method of sarcogrelate hydrochloride, in particular to a method for preparing sarcogrelate hydrochloride by using 2-[2-(3-methoxyphenyl)ethyl]phenol as a raw material. 2. Background technology [0002] Sarpogrelate hydrochloride (sarpogrelatehydrochloride), the chemical name is succinic acid mono[2-(dimethylamino)-1-[[2-[2-(3-methoxyphenyl)ethyl]phenoxy] Methyl] ethyl] ester hydrochloride, 5-HT developed by Japan Mittsubishi Tanabe Pharma 2 Receptor antagonists and platelet aggregation antagonists, first launched in Japan in 1993, are mainly used clinically to improve ischemic symptoms such as chronic thromboangiitis obliterans accompanied by ulcers, pain and cold sensation. [0003] The synthetic method of traditional sargrel hydrochloride is to be by 2-[2-(3-methoxyphenyl) ethyl] phenol and epichlorohydrin, under using sodium hydride and anhydrous condition, make [[2- [2-(3-Methoxyphenyl)ethyl]phenoxy]methy...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C219/06C07C213/06C07C213/08
Inventor 余世春范石虎
Owner ANHUI AN TECH MEDICAL & BIOLOGICAL TECH
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