Method for preparing industrial safinamide mesylate

A technology of safinamide mesylate and propionamide, which is applied in the field of industrialized preparation of safinamide mesylate, can solve the problems of complicated operation, high cost, large environmental pollution and the like, and achieves simple post-processing and low cost , Environmentally friendly effect

Inactive Publication Date: 2016-12-14
合肥远志医药科技开发有限公司
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Problems solved by technology

However, the current industrialized preparation method is complex in operation, high in cost, and causes great environmental pollution.

Method used

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  • Method for preparing industrial safinamide mesylate

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Embodiment 1

[0013] 1. Preparation of 4-(3-fluorobenzyloxy)benzaldehyde (SFXA01):

[0014] Add 15.2g (124.5mmol) of p-hydroxybenzaldehyde, 17.2g (124.5mmol) of potassium carbonate and 2.0g (12mmol) of potassium iodide to 170ml of absolute ethanol, stir for 15min, and add 17.3ml (141.7mmol) of 3-fluorochlorobenzyl dropwise. ), heated to reflux for 6h. Filter, wash the filter cake with absolute ethanol (15ml×3), combine the filtrate and lotion, concentrate under reduced pressure, add 60ml of toluene and 20ml of water to the remaining light yellow oil, stir for 30min, let stand to separate layers, and separate the toluene layer , concentrated under reduced pressure, and the residue was recrystallized from toluene-n-hexane (1:1) to obtain 26.1 g (91%) of 4-(3-fluorobenzyloxy)benzaldehyde as a white solid, mp 43.8-43.9°C.

[0015] 2. Preparation of (S)-2-[4-(3-fluorobenzyloxy)benzylamino]propionamide (SFXA02):

[0016] (S)-2-alanine methyl ester hydrochloride 15.4g (110mmol), 4-(3-fluorobenzy...

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Abstract

The invention relates to a method for preparing industrial safinamide mesylate, and belongs to the technical field of organic synthesis. The method comprises the steps that a compound 3-fluorobenzylchloride and a compound p-hydroxy benzaldehyde react to generate a compound 4-(3-fluorophenyl)benzaldehyde, then the compound 4-(3-fluorophenyl)benzaldehyde and (S)-2-amino methyl propionate hydrochloride are condensed to prepare a compound (S)-2-[4-(3-fluorophenyl)benzylamine]propanamide, the compound (S)-2-[4-(3-fluorophenyl)benzylamine]propanamide is subjected to catalytic hydrogenation reducing with Pd/C, and the product is recrystallized through methylbenzene and then salified with methanesulfonic acid. A new industrial synthesis selection mode is provided, the synthesis mode has the advantages of being easy and convenient to operate, simple in aftertreatment, lower in cost, environmentally friendly and the like, the high-quality target product can be obtained, and industrial production is promoted.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of industrialized safinamide methanesulfonate. Background technique [0002] Safinamide mesilate, chemically named (S)-2-[4-(3-fluorobenzyloxy)benzylamino]propionamide mesilate, was developed by Newron Pharmaceuticals Anti-Parkinson's disease drugs. This product has a variety of mechanisms of action, not only highly selective and reversible inhibition of monoamine oxidase B (MAO-B), but also inhibition of dopamine reuptake, blocking voltage-dependent sodium channels, regulating calcium channels, thereby inhibiting the release of glutamate . Safinamide has high bioavailability in the central nervous system, clinically shown that it can improve the motor and cognitive functions of patients with Parkinson's disease, prevent patients from motor disorders, and has good tolerance. However, the current industrialized preparation method is complex in ope...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/12C07C237/06C07C45/64C07C47/575C07C309/04C07C303/32
CPCC07C231/12C07C45/64C07C303/32
Inventor 曹亮亮蒋维胡孟奇
Owner 合肥远志医药科技开发有限公司
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