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Method for synthesizing butenafine

A butenafine and synthetic method technology, applied in the field of pharmaceutical chemical synthesis, can solve the problems of low reaction yield and many side reactions, and achieve the effects of simple steps, convenient operation and few by-products

Active Publication Date: 2018-05-18
SHANDONG BOYUAN PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Yet, in the preparation process of N-methyl-1-naphthylmethylamine, 1-chloromethylnaphthalene and monomethylamine reaction yield are lower, and side reaction is more

Method used

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  • Method for synthesizing butenafine
  • Method for synthesizing butenafine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment 1: add purified water 1000ml in 2000ml reaction bottle, slowly add 36g monomethylamine in water, then add salt of wormwood 312g in reaction bottle, add 1-chloromethyl naphthalene 100g respectively in two constant pressure funnels, 109 g of p-tert-butyl benzyl chloride, temperature control 10-20 ° C, slowly drop 1-chloromethylnaphthalene and p-tert-butyl benzyl chloride at the same time, control the rate of addition, so that 1-chloromethyl naphthalene and p-tert-butyl chloride The benzyl was added dropwise at the same time, and then the temperature was controlled at 10-20°C and the reaction was kept for 4 hours. Add 500ml of chloroform to the reaction solution to extract the reaction solution, control the temperature of the water bath at 60°C and concentrate the organic layer to dryness under reduced pressure, add 480ml of isopropanol to the residue, heat to 60°C, stir for 30 minutes, cool down to below 10°C, Crystallize for 30 minutes, filter with suction to ...

Embodiment 2

[0026] Example 2: Add 1000ml of purified water to a 2000ml reaction flask, slowly add 40g of monomethylamine to the water, then add 353.8g of potassium carbonate to the reaction flask, and add 110.5 g of 1-chloromethylnaphthalene to two constant pressure funnels g, p-tert-butyl benzyl chloride 116.9g, temperature control 10-20 ℃, slowly drop 1-chloromethylnaphthalene and p-tert-butyl benzyl chloride at the same time, control the rate of addition, make 1-chloromethyl naphthalene and p-tert The butyl benzyl chloride was all added dropwise at the same time, and then the temperature was controlled at 10-20°C and the reaction was kept for 4 hours. Add 500ml of chloroform to the reaction solution to extract the reaction solution, control the temperature of the water bath at 60°C and concentrate the organic layer to dryness under reduced pressure, add 480ml of isopropanol to the residue, heat to 60°C, stir for 30 minutes, cool down to below 10°C, Crystallize for 30 minutes, filter wi...

Embodiment 3

[0027] Embodiment 3: Add purified water 1000ml in 2000ml reaction bottle, slowly add 38g monomethylamine in water, then add potassium carbonate 328.5g in reaction bottle, add 1-chloromethyl naphthalene 103g respectively in two constant pressure funnels , p-tert-butyl benzyl chloride 111g, temperature control 10-20 ° C, slowly drop 1-chloromethylnaphthalene and p-tert-butyl benzyl chloride at the same time, control the rate of addition, so that 1-chloromethyl naphthalene and p-tert-butyl The benzyl chloride was all added dropwise at the same time, and then the temperature was controlled at 10-20°C and the reaction was kept for 4 hours. Add 500ml of chloroform to the reaction solution to extract the reaction solution, control the temperature of the water bath at 60°C and concentrate the organic layer to dryness under reduced pressure, add 480ml of isopropanol to the residue, heat to 60°C, stir for 30 minutes, cool down to below 10°C, Crystallize for 30 minutes, filter with sucti...

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Abstract

The invention provides a method for synthesizing butenafine. The method includes the steps of adding monomethylamine to a solvent and then adding an acid-binding agent; slowly dropping 1-chloromethylnaphthalene and p-tert-butylchlorobenzyl chloride at the same time, controlling the dropping rate so that dropping of 1-chloromethylnaphthalene and p-tert-butylbenzyl chloride can be completed at the same time, and then controlling the temperature to be 10-20 DEG C to perform a thermal insulation reaction for 4 hours; extracting a reaction solution with chloroform, concentrating an organic layer under reduced pressure to dryness, and adding isopropanol to residues for crystallization to obtain butenafine. The method has the advantages of having convenient operation, less by-products, high yieldand short production cycle and being conducive to industrial production.

Description

technical field [0001] The invention relates to the field of pharmaceutical chemical synthesis, in particular to a method for synthesizing butenafine. Background technique [0002] Butenafine hydrochloride (butenafine hydrochloride, 1), the chemical name is N-(4-tert-butylphenyl)-N-methyl-1-naphthylmethylamine hydrochloride, is an olefin developed by Japan Research Corporation. Propylamine antifungal drug, and was first listed in Japan in 1992. Butenafine is a benzylamine derivative, and its mechanism of action is to selectively inhibit fungal squalene cyclooxygenase, interfere with the biosynthesis of ergosterol in fungal cell walls, affect the lipid metabolism of fungi, and make fungi Cell damage or death to play a bactericidal and bacteriostatic effect. It is mainly used for the local treatment of tinea pedis, tinea corporis, and jock itch caused by tinea flocculus, rubrum, trichophyton mentagrophytes, and alopecia areata; it is used for skin fungal infections, such as ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/30C07C209/00C07C209/84
CPCC07C209/00C07C209/84C07C211/30
Inventor 赵孝杰苏曼
Owner SHANDONG BOYUAN PHARM CO LTD
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