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Preparation method of terbinafine hydrochloride

A technology of terbinafine hydrochloride and monomethylamine, applied in the field of medicine, can solve the problems of unsuitability for industrialized production, high production cost, rare raw materials, etc., and achieve the effects of simple production steps, low price, and easily available raw materials

Active Publication Date: 2013-01-30
山东艾兰药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] In the above synthetic routes, either the yield is low, or the raw materials are rare, the production cost is high, and it is not suitable for industrial production

Method used

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  • Preparation method of terbinafine hydrochloride
  • Preparation method of terbinafine hydrochloride
  • Preparation method of terbinafine hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Step 1: Synthesis of (E)-1-methylamino-3-chloro-propene

[0032] Add 200 grams of monomethylamine aqueous solution (30%) into a 500ml reaction bottle, start stirring, cool down to 0°C, add 0.5 grams of tributylammonium bromide, and drop 50 grams of (E)-1,3 dichloropropene , slowly raised to 20°C, reacted for 4 hours, monitored (E)-1-methylamino-3-chloro-propene remaining 3%, continued to rise to 25°C for 2 hours, remained 1.3%, separated. The product was in the lower layer, and the residual monomethylamine was washed with water, then 5 g of sodium sulfate was added as a desiccant, dried, and 45 g of the product was obtained by suction filtration, with a content of 97.5% and a yield of 92.5%. For this step reaction, the sealing performance of the reaction vessel is required to be better.

[0033] Step 2: Synthesis of (E)-N-(6,6-dimethyl-2-hepten-4-ynyl)methanamine

[0034] Put 45 grams of (E)-1-methylamino-3-chloro-propene in step 1 into the reaction flask, add 100 gra...

Embodiment 2

[0038] Step 1: Synthesis of (E)-1-methylamino-3-chloro-propene

[0039]Add 380 grams of monomethylamine aqueous solution (30%) into a 1000ml reaction bottle, start stirring, cool down to 2°C, add 1.0 grams of tributylammonium bromide, add dropwise 100 grams of (E)-1,3 dichloropropene , slowly raised to 20°C, reacted for 3 hours, monitored (E)-1-methylamino-3-chloro-propene remaining 3.8%, continued to rise to 25°C for 2.5 hours, remained 1.2%, separated, the product was in the lower layer , washed the residual monomethylamine with water, then added 10 grams of desiccant sodium sulfate, dried, and suction filtered to obtain 90.5 grams of the product, with a content of 97.3% and a yield of 92.7%. For this step reaction, the sealing performance of the reaction vessel is required to be better.

[0040] Step 2: Synthesis of (E)-N-(6,6-dimethyl-2-hepten-4-ynyl)methanamine

[0041] Put 90.5 grams of (E)-1-methylamino-3-chloro-propene in step 1 into the reaction flask, add 190 grams...

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PUM

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Abstract

The invention discloses a preparation method of terbinafine hydrochloride, and belongs to the technical field of medicine. According to the method, a monomethylamine aqueous solution and (E)-1, 3 dichloropropene are taken as materials to react to obtain (E)-1-methylamino-3-chlorine-propylene; then (E)-1-methylamino-3-chlorine-propylene reacts with tertiary butyl acetylene to obtain (E)-N-(6, 6-dimethyl-2-heptylene-4-alkynyl) methylamine; and then the (E)-N-(6, 6-dimethyl-2-heptylene-4-alkynyl) methylamine reacts with 1-chlorine-methylnaphthalene to obtain terbinafine, and hydrochloric acid is added for salification to obtain terbinafine hydrochloride. According to the method, materials are easy to get, the cost is low, the preparation method is simple, the yield is high, and the method is suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of terbinafine hydrochloride, which belongs to the technical field of medicine. Background technique [0002] Terbinafine hydrochloride, the chemical name is: (E)-N-(6,6-dimethylhept-2-en-4-ynyl)-N-methyl-1-naphthylmethylamine hydrochloride ( English name: N,6,6-Trimethyl-N-(naphthalen-1-ylmethyl)hept-2-en-4-yn-1-amine hydrochloride), molecular formula C 21 h 25 N·HCl. Its structural formula is shown below. [0003] [0004] Terbinafine hydrochloride belongs to the allylamine antifungal drugs and is one of the seven new synthetic antifungal drugs listed in the 1990s. Because of its wide antibacterial spectrum, bactericidal, high curative effect, and low toxic and side effects, it has attracted worldwide attention. Mainly used for the treatment of onychomycosis, tinea pedis, tinea manuum, tinea corporis, jock itch and tinea versicolor, vaginal candida infection and other diseases. Terbinafine entere...

Claims

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Application Information

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IPC IPC(8): C07C211/30C07C209/08
Inventor 张志强尚林峰苏曼
Owner 山东艾兰药业有限公司
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