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Synthesis method of butenafine hydrochloride

A technology of butenafine hydrochloride and a synthesis method, which is applied in the field of drug synthesis, can solve the problems of low detection limit of finished products, harsh reaction conditions, low production cost, etc., and achieves the advantages of being suitable for industrial production, few reaction steps, and high product yield. Purity-enhancing effect

Pending Publication Date: 2021-10-12
LUNAN PHARMA GROUP CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0027] (1) Carry out N-alkylation reaction with halogenated alkanes, easily produce N-overalkylation impurities, need further refining;
[0028] (2) The reductive ammoniation process needs to use expensive ruthenium as a catalyst, which makes the production cost higher;
[0030] (4) N-alkyl side chains are introduced through amide reduction, but lithium aluminum hydride or organosilane compounds / non-metallic boron compounds need to be used as reducing agents, which not only requires harsh reaction conditions, but also makes the production cost higher;
[0031] (5) The reductive ammoniation process requires the application of highly toxic heavy metal cadmium compounds, making the detection limit of the finished product extremely low
[0032] In view of the many problems existing in the prior art, it is still a problem to be solved at present to study and find a mild reaction condition, simple and convenient operation process, high product yield, high purity, and low production cost suitable for industrialized production of butenafine

Method used

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  • Synthesis method of butenafine hydrochloride
  • Synthesis method of butenafine hydrochloride
  • Synthesis method of butenafine hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Under argon protection, the [Cp*IrCl 2 ] 2 (1.59g, 0.002mol), sodium bicarbonate (0.42g, 0.005mol), N-methyl-1-naphthylmethylamine (17.12g, 0.10mol), p-tert-butylbenzyl alcohol (16.42g, 0.10mol) 1. Deionized water (150mL) was added to the Schlenk device, sealed and placed in a temperature-controlled oil bath at 110°C to react for 8 hours. After the reaction was completed, the reaction solution was cooled to room temperature, and dichloromethane (50mL×3) was added for extraction, and the extracts were combined Concentrate under reduced pressure to dryness, add HCl / methanol (150mL, 2mol / L) to form a salt, continue to stir and crystallize for 2 to 3 hours, then filter, and the filter cake is dried under reduced pressure to become butenafine hydrochloride, with a yield of 96.3%. HPLC: 99.89%.

Embodiment 2

[0068] Under nitrogen protection, the [Cp*IrCl 2 ] 2 (1.59g, 0.002mol), sodium bicarbonate (0.42g, 0.005mol), N-methyl-1-naphthylmethylamine (17.12g, 0.10mol), p-tert-butylbenzyl alcohol (18.07g, 0.11mol) 1. Deionized water (150mL) was added to the Schlenk device, sealed and placed in a temperature-controlled oil bath at 110°C to react for 8 hours. After the reaction, the reaction solution was cooled to room temperature, and dichloromethane (50mL×3) was added for extraction, and the combined extraction liquid and concentrated to dryness under reduced pressure, added HCl / methanol (300mL, 0.5mol / L) to form a salt, continued to stir and crystallize for 2 to 3 hours, then filtered, and the filter cake was dried under reduced pressure to become butenafine hydrochloride, with a yield of 96.8 %, HPLC: 99.80%.

Embodiment 3

[0070] Under argon protection, the [Cp*IrCl 2 ] 2 (1.59g, 0.002mol), sodium bicarbonate (0.42g, 0.005mol), N-methyl-1-naphthylmethylamine (17.12g, 0.10mol), p-tert-butylbenzyl alcohol (18.89g, 0.115mol) 1. Deionized water (150mL) was added to the Schlenk device, sealed and placed in a temperature-controlled oil bath at 110°C to react for 8 hours. After the reaction, the reaction solution was cooled to room temperature, and dichloromethane (50mL×3) was added for extraction, and the combined extraction and concentrated to dryness under reduced pressure, adding HCl / 1,4-dioxane (150mL, 2mol / L) to form a salt, continuing to stir and crystallize for 2 to 3 hours, and then filtering, and the filter cake was dried under reduced pressure to become Butei hydrochloride Nafine, yield 95.8%, HPLC: 99.76%.

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Abstract

The invention belongs to the technical field of medicine synthesis, and particularly relates to a synthesis method of butenafine hydrochloride. The method comprises steps: adopting N-methyl-1-naphthyl methylamine and p-tert-butyl benzyl alcohol as raw materials, synthesizing butenafine under the action of a catalyst, and salifying with an HCl / organic solvent, filtering, and drying a filter cake under reduced pressure to obtain butenafine hydrochloride. The product obtained by the method has higher purity and yield.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis, in particular to a method for synthesizing butenafine hydrochloride. Background technique [0002] Butenafine hydrochloride (butenafine hydrochloride), the chemical name is N-(4-tert-butylphenyl)-N-methyl-1-naphthylmethylamine hydrochloride, is an allylamine developed by Japan Research Co., Ltd. Antifungal drug, and was first listed in Japan in 1992 under the trade name Mentax. This product can highly selectively inhibit the activity of fungal squalene epoxidase, and inhibit the biosynthesis of squalene and ergosterol in fungi, thereby destroying the formation of fungal cell membranes and leading to the death of fungi. It has the characteristics of broad antibacterial spectrum, high antibacterial activity, low recurrence rate, and small side effects, and is widely used in clinical practice. Its chemical structure is shown below: [0003] [0004] The synthetic technique about but...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/68C07C211/30
CPCC07C209/68C07C211/30
Inventor 于成彬张乃华
Owner LUNAN PHARMA GROUP CORPORATION
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