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Method for synthesizing (R)-3-ethyl piperidine hydrochloride

A technology of ethyl acetate hydrochloride and pyridine ethyl acetate ammonium salt, which is applied in the field of drug synthesis and chemical industry, can solve the problems that microwave technology is not suitable for large-scale production and difficult recovery, and achieves easy storage and transportation, stable properties, The effect of easy purification

Inactive Publication Date: 2010-06-09
EAST CHINA NORMAL UNIV
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Problems solved by technology

Due to the use of precious metal Pt, recycling is also difficult, and microwave technology is also not suitable for large-scale production

Method used

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  • Method for synthesizing (R)-3-ethyl piperidine hydrochloride

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Embodiment 1

[0037] The first step. Synthesis of ethyl 3-pyridine acetate (II)

[0038] At room temperature, add 3-pyridineacetic acid hydrochloride (250.0g, 1.44mol) into a 5L single-neck round bottom flask, then add 2.5L ethanol, and stir mechanically; under ice-water bath conditions, slowly add 35ml of SOCl 2 (51.4g, 0.43mol), after dropping, remove the ice-water bath, and heat to reflux overnight. TLC detects the reaction, after the reaction is complete, spin off the solvent ethanol to obtain a white solid, dissolve it with 2M sodium carbonate solution, adjust the solution to alkalinity, extract with ethyl acetate, wash with saturated sodium chloride solution, separate the layers, and combine the organic phases, Dry over anhydrous sodium sulfate and spin dry to obtain 230.0 g of compound (II) as a yellow oil with a yield of 96.6%.

[0039] Second step. Synthesis of (N-benzyl)-3-pyridine ethyl acetate ammonium chloride (III)

[0040] At room temperature, 3-pyridine ethyl acetate (230....

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Abstract

The invention relates to a method used for synthesizing (R)-3-ethyl piperidine hydrochloride. 3-pyridineacetic acid hydrochloride is used as a raw material, a target product of the (R)-3-ethyl piperidine hydrochloride which has the function of slight moisture absorption and is convenient to store is obtained by total five steps of reactions of esterification, quaternary ammonium salt synthesis, Pd / C / H2 reduction, L-(+)-mandelic acid splitting and hydrochloride synthesis, and the optical purity of the (R)-3-ethyl piperidine hydrochloride reaches more than 99%. The invention has the advantages of high selectivity, high yield, low cost, simple and convenient operation and purification method and good economic benefit and is more suitable for industrialized production.

Description

technical field [0001] The present invention relates to a kind of method of (R)-3-piperidine ethyl acetate hydrochloride. (R)-3-piperidine ethyl acetate hydrochloride is an intermediate used in the synthesis of drugs for treating neurological diseases, and belongs to the technical field of drug synthesis and chemical engineering. Background technique [0002] The piperidine ring is the target of many analgesic drugs, and has a wide range of scientific research and medicinal value. (R)-3-Piperidine ethyl acetate is also an important drug intermediate, mainly used in the synthesis of a variety of drugs for the treatment of neurological diseases, such as anti-epilepsy and convulsions, etc. research hotspots. At present, the synthesis report of this compound is blank in China. [0003] Patent WO 9854179A1 discloses a method for synthesizing (R)-3-piperidine ethyl acetate, which uses 3-pyridine ethyl acetate as a raw material, and then directly uses 10% of the substrate at a m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/34
Inventor 胡文浩阚洪柱朱映光任白燕马海坤杨琍苹
Owner EAST CHINA NORMAL UNIV