Preparation method of Terbinafine hydrochloride

A technology of terbinafine hydrochloride and naphthylmethylamine hydrochloride is applied in the field of preparation of terbinafine hydrochloride, can solve the problems of high reaction temperature, high price, long reaction time and the like, and achieves complete reaction , the effect of shortened reaction time, cheap and easy-to-obtain raw materials

Inactive Publication Date: 2010-10-27
YANGTZE RIVER PHARMA GRP BEIJING HAIYAN PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In the above method, the price of 1-bromo-6,6-dimethyl-2-hepten-4-yne is relatively high, or the reaction temperature is too high, and the reaction time is too long, all of which have certain limitations.

Method used

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  • Preparation method of Terbinafine hydrochloride

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Experimental program
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Embodiment

[0020] At room temperature, add 650ml of N,N-dimethylformamide into a 1000ml three-necked flask, add 7.5 grams (0.05 moles) of sodium iodide, stir to dissolve, add dropwise 78.5 grams (0.5 moles) of 1-chloro-6,6 -Dimethyl-2-hepten-4-yne, reacted for 1 hour. Add 106 grams (1 mole) Na in turn to the reaction solution 2 CO 3 , 104 grams (0.5 moles) of N-methyl-1-naphthylmethylamine hydrochloride, reacted at 20° C.-30° C. for 4 hours.

[0021] The solid in the reaction liquid was removed by filtration, and the concentrated brown liquid was added to 600 ml of ethyl acetate, mixed well, washed with an appropriate amount of water, the water layer was separated, the organic layer was dried, and concentrated to obtain 140 g of brown liquid. With 500 ml of absolute ethanol, under stirring, an appropriate amount of dry hydrogen chloride was introduced into the reaction solution, stirred at room temperature for half an hour, and concentrated to obtain 200 g of a yellow solid.

[0022] ...

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Abstract

The invention relates to a preparation method of Terbinafine hydrochloride, which comprises the following steps: dissolving a certain amount of catalyst, i.e. sodium iodide (or potassium iodide) in an organic solvent, adding 1-chloro-6,6-dimethyl-2-heptylene-4-alkyne, sequentially adding alkali and N-methyl-1-naphthalene methylamine hydrochloride, carrying out condensation at 10-40 DEG C, salifying the obtained product in an alcohol system with hydrogen chloride to obtain the Terbinafine hydrochloride, and carrying out recrystallization in an alcohol/water mixed solution to obtain the qualified product. In the method, the raw materials are cheap and easily-acquired, the reaction is complete, and the reaction time is greatly shortened. Therefore, the method is completely suitable for industrialized mass production.

Description

technical field [0001] The invention relates to the technical field of drug synthesis, in particular, the invention relates to a preparation method of terbinafine hydrochloride. Background technique [0002] Terbinafine hydrochloride ((E)-N-(6,6-Dimethyl-2-hepten-4-yne)-N-methyl-1-naphthylmethylamine hydrochloride) is allylamine A class of broad-spectrum antifungal drugs for the treatment of tinea manuum, tinea pedis, tinea corporis, jock itch and tinea versicolor caused by sensitive fungi. It can specifically interfere with the early biosynthesis of fungal sterols, selectively inhibit the activity of fungal squalene epoxidase, and hinder the squalene epoxidation reaction in the process of fungal cell membrane formation, so as to kill or Inhibits the action of fungi. [0003] Terbinafine hydrochloride has a large market demand, and people are eager to have a simple, high-yield, economical method that can be easily produced on a large scale. [0004] There are many methods...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/30B01J27/08A61P31/10
Inventor 张培龙石和鹏侯鹏李玉宽宋志涛周津梅
Owner YANGTZE RIVER PHARMA GRP BEIJING HAIYAN PHARMA
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