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Preparation method for sarpogrelate hydrochloride

A technology of sarcogrelate hydrochloride and methoxyphenyl, which is applied in the field of preparation of sarcogrelate hydrochloride, can solve problems such as difficult operation and poor quality stability, and achieve the effect of stable quality and easy operation

Inactive Publication Date: 2012-03-14
TIANJIN KELIN CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] "Pharmaceutical Chemistry" J.Med.Chem.1990.33.1818-1823 discloses the synthesis of sarcogrelate hydrochloride, its intermediate [2-[2-3-(dimethylamino)-2-hydroxypropoxy] Phenyl] ethyl] benzene hydrochloride adopts in 30mlDMF, adds NaH under ice bath, drips the solution that is made up of 2-[2-(3-methoxyphenyl) ethyl]phenol and 30mlDMF, epoxy Chloropropane (23.4g, 0.25mol) is added to the solution and prepared by mixing and stirring at room temperature. This method has the problems of difficult operation and poor quality stability

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] In a solution of 2.48g NaOH (0.0595mol) and 100ml 95% ethanol, add a solution consisting of 11.4g (0.05mol) 2-[2-(3-methoxyphenyl)ethyl]phenol and 30ml 95% ethanol , 28g (0.03027mol) of epichlorohydrin was added to the solution and stirred at room temperature for 6hr;

[0041] The solution was filtered, and the filtrate was concentrated under reduced pressure. The residue was added with 72ml of water, extracted with dichloromethane, dried, and vacuum distilled into an oily substance, which was [[2-(3-methoxyphenyl)ethyl]phenoxy] Methyl]ethylene oxide;

[0042] 13.95g (0.049mol) of the above oily substance was dissolved in 65ml of tetrahydrofuran, 67ml (0.049mol) of 33% dimethylamine aqueous solution was added dropwise below 10°C, after the addition, the reaction was carried out at room temperature for 9hr.

[0043] Concentrated under reduced pressure, the residue was extracted with isopropyl ether, washed with water, dried, and concentrated to dryness. The residue was dissolv...

Embodiment 2

[0047] To a solution of 3.4gKOH (0.0595mol) and 100ml 95% ethanol, add a solution consisting of 11.4g (0.05mol) 2-[2-(3-methoxyphenyl)ethyl]phenol and 30ml 95% ethanol , 28g (0.03027mol) of epichlorohydrin was added to the solution and stirred at room temperature for 6hr;

[0048] The solution was filtered, and the filtrate was concentrated under reduced pressure. The residue was added with 72ml of water, extracted with dichloromethane, dried, and vacuum distilled into an oily substance, which was [[2-(3-methoxyphenyl)ethyl]phenoxy] Methyl]ethylene oxide;

[0049] 13.95g (0.049mol) of the above oily substance was dissolved in 65ml of tetrahydrofuran, 67ml (0.049mol) of 33% dimethylamine aqueous solution was added dropwise below 10°C, after the addition, the reaction was carried out at room temperature for 9hr.

[0050] Concentrated under reduced pressure, the residue was extracted with isopropyl ether, washed with water, dried, and concentrated to dryness. The residue was dissolved ...

Embodiment 3

[0053] To a solution of 2.48g NaOH (0.0595mol) and 100ml 90% ethanol, add a solution consisting of 11.4g (0.05mol) 2-[2-(3-methoxyphenyl)ethyl]phenol and 30ml 90% ethanol , 28g (0.03027mol) of epichlorohydrin was added to the solution and stirred at room temperature for 6hr;

[0054] The solution was filtered, the filtrate was concentrated under reduced pressure, the residue was added with 80ml of water, extracted with dichloromethane, dried, and vacuum distilled into an oily substance, which was [[2-(3-methoxyphenyl)ethyl]phenoxy] Methyl]ethylene oxide;

[0055] Dissolve 13.95g (0.049mol) of the above oily substance in 70ml of tetrahydrofuran, add 67ml (0.049mol) of 35% dimethylamine aqueous solution dropwise below 10°C, after addition, react at room temperature for 9.5hr.

[0056] Concentrated under reduced pressure, the residue was extracted with isopropyl ether, washed with water, dried, and concentrated to dryness. The residue was dissolved in ethyl acetate, and 30% HCL was add...

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Abstract

The invention discloses a preparation method for sarpogrelate hydrochloride. The method comprises the steps of preparation of the intermediate [[2-(3-methoxyphenyl)ethyl]phenoxyl]methyl]oxirane, 1-dimethylamino-3-[2-[2-(3-methoxyphenyl)ethyl]phenoxyl]2-propyl alcohol and a finished product in order. According to the invention, ethanol with a concentration of 95% is used as a solvent, and substituted sodium hydride is changed into sodium hydroxide or potassium hydroxide or the like; therefore, cost is reduced, operation is simple, and the finished product has stable quality.

Description

Invention field [0001] The invention relates to a preparation method of sargresil hydrochloride, and belongs to the field of medicinal chemistry. Background technique [0002] Sarpogrelate hydrochloride (1), chemical name 2-(dimethylamino)-1-{[2-(3-methoxyphenyl)phenoxy]methyl}ethylsuccinic acid Monoester hydrochloride is a 5-HT2 receptor antagonist and platelet aggregation antagonist developed by Mitsubishi Tanabe Pharma in Japan. It was first launched in Japan in 1993. It is clinically used to improve chronic thrombosis with ulcers, pain and cold sensation. Ischemic symptoms such as vasculitis obliterans. [0003] "Pharmaceutical Chemistry" J.Med.Chem.1990.33.1818-1823 discloses the synthesis of sagrelate hydrochloride and its intermediate [2-[2-3-(dimethylamino)-2-hydroxypropoxy] Phenyl] ethyl] benzene hydrochloride in 30ml DMF, add NaH in an ice bath, drop by drop a solution consisting of 2-[2-(3-methoxyphenyl)ethyl]phenol and 30ml DMF, epoxy Chloropropane (23.4g, 0.25mol) w...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C219/06C07C213/06
Inventor 王浩王新磊
Owner TIANJIN KELIN CHEM
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