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Amorolfine hydrochloride preparation method

A compound and catalyst technology, applied in the field of preparation of amorolfine hydrochloride, can solve the problems of long steps, high cost, low yield and the like, and achieve the effects of low cost, good product quality and high yield

Active Publication Date: 2018-12-14
JIANGSU LEEWAY BIOLOGICAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The existing process routes generally have the problems of long steps or low yields and high costs. It is urgent to find a new process with low production cost, simple process and suitable for industrial production.

Method used

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  • Amorolfine hydrochloride preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Synthesis of (E)-1-((2R,6S)-2,6-dimethylmorpholine)-2-dimethyl-3-phenyl-2-en-1-one compound formula Ⅲ

[0041]

[0042] Compound formula IIa (15.00g, 0.092mol), HBTU (34.89g, 0.092mol), N,N-diisopropylethylamine (23.78g, 0.184mol) were added to N,N-dimethylacetamide (150mL), stir well. After reacting at 25°C for 0.5h, cis-2,6-dimethylmorpholine (12.73g, 0.110mol) was added and reacted at 25°C for 2-3h. Cool to room temperature, add the reaction solution into water, dichloromethane extraction and separation, and the dichloromethane phase was extracted and separation with saturated brine, the organic layer was taken, and then concentrated to dryness to obtain a yellow oil compound formula III with a yield of 95.36 %, HPLC detection purity 98.79%.

Embodiment 11

[0044] Referring to the method of Example 1, the intermediate III reaction solvent was screened and optimized, and the experimental results are shown in the table below.

[0045] serial number

Embodiment 12

[0047] Referring to the method of Example 1, the condensing agent for the reaction of intermediate III was screened and optimized, and the experimental results are shown in the table below.

[0048] serial number

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Abstract

The invention provides an amorolfine hydrochloride preparation method which specifically comprises the following steps: putting a compound of formula IIa shown in the specification into an organic solvent, further putting an amidation catalyst, carrying out a stirring reaction, further adding cis-2,6-dimethyl morpholine, and carrying out a reaction so as to obtain a compound III; carrying out backflow stirring on the compound III in absolute methanol, adding magnesium chips in batches, and carrying out a reaction so as to obtain a compound IV; carrying out a reaction on the compound IV under the action of a reducing agent, thereby obtaining a compound V. The method is novel in process route, cheap and easy in raw material obtaining, low in cost, simple in process operation, short in production cycle, gentle in reaction condition, high in yield, good in product quality and applicable to industrial production.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical production, in particular to a preparation method of amorolfine hydrochloride. Background technique [0002] Amorolfine hydrochloride (amorolfine hydrochloride), the chemical name is cis-4-[3-[4-(1,1-dimethyl-propyl)phenyl]-2-methylpropyl]-2,6 -Dimethyl-morpholine hydrochloride, the CAS registration number is 78613-38-4, and its chemical structure is as follows: [0003] [0004] The preparation method of following several amorolfine hydrochloride has been reported in the prior art: [0005] US7795425 invention patent uses 2-methylcinnamaldehyde as raw material to condense with cis-2,6-dimethylmorpholine to obtain cis-4-(3-phenyl-2-methylpropyl)-2,6-di Methyl-morpholine hydrochloride, and 2-methyl-2-chlorobutane, catalyzed by acid, undergoes Heck reaction to obtain amorolfine. This method uses an expensive palladium catalyst, which is not conducive to industrial scale production. The...

Claims

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Application Information

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IPC IPC(8): C07D265/30
CPCC07D265/30
Inventor 张孝清包金远刘宝黄辉戴恩
Owner JIANGSU LEEWAY BIOLOGICAL TECH
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