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New method for synthesizing Gabapentin hydrochloride

A new synthesis technology of gabapentin hydrochloride, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve problems such as high equipment requirements, environmental pollution, poor safety, etc., and achieve industrialized production with short routes. , less toxic effect

Inactive Publication Date: 2006-02-01
CHANGCHUN DISCOVERY SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The invention provides a new synthesis method of gabapentin hydrochloride to solve the problems of poor safety, high equipment requirements and serious environmental pollution in the current synthesis process

Method used

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  • New method for synthesizing Gabapentin hydrochloride
  • New method for synthesizing Gabapentin hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Embodiment 1: the preparation of spiro[3,5]-2-nonanone III

[0015] To methylenecyclohexane IV (0.96g, 10mmol), zinc powder (0.768g, 12mmol), 40mL ether solution, dropwise add trichloroacetyl chloride (2.2g, 12mmol) 10mL ether solution, keep the temperature at 20°C , continue ultrasonication for 3-4 hours, the temperature is gradually raised from 20°C to 40°C, and excess zinc powder is filtered off, the filtrate is washed with saturated ammonium chloride solution, sodium bicarbonate solution, and salt water, and diethyl ether is evaporated with a rotary evaporator. 1.94 g of the compound 1,1-dichlorospiro[3,5]-2-nonanone was obtained.

[0016] The compound 1,1-dichlorospiro[3,5]-2-nonanone (1.94g, 9.35mmol) and zinc powder (1.92g, 30.mmol) were stirred in 20mL of glacial acetic acid at 20-30°C for 10 hours, Thin-layer chromatography TLC showed that the substrate disappeared, filtered with suction, added 50 mL of water to the filtrate, extracted three times with n-hexan...

Embodiment 2

[0022] The preparation of spiro[3,5]-2-nonanone III is the same as in Example 1

[0023] Preparation of 2-aza-spiro[4,5]-3-decanone II

[0024] At room temperature, hydroxylamine-O-sulfonic acid (0.992g, 7.5mmol) was slowly added to a solution of compound III (765mg, 5mmol) in 10mL of formic acid, stirred until the solution was transparent, heated to reflux for 4.5 hours, thin layer chromatography TLC It showed that compound III disappeared, cooled to room temperature, poured into 50mL saturated sodium bicarbonate solution, adjusted to weak alkalinity, extracted with chloroform (15mL×3), washed the organic phase with saturated brine, dried over anhydrous magnesium sulfate, and used a rotary evaporator The solvent was distilled off to obtain a yellow oil, which was subjected to column chromatography (eluent: n-hexane: ethyl acetate = 3:1) to obtain 0.4 g of compound II.

[0025] The preparation of 1-(aminomethyl)-cyclohexylacetic acid hydrochloride I

[0026] Compound 2-aza-s...

Embodiment 3

[0028] The preparation of spiro[3,5]-2-nonanone III is the same as in Example 1

[0029] Preparation of 2-aza-spiro[4,5]-3-decanone II

[0030] At room temperature, hydroxylamine-O-sulfonic acid (1.32g, 10mmol) was slowly added to a solution of compound III (765mg, 5mmol) in 10mL of formic acid, stirred until the solution was transparent, heated to reflux for 4 hours, thin layer chromatography TLC showed Compound III disappeared, cooled to room temperature, poured into 50ml of saturated sodium bicarbonate solution, adjusted to weak alkalinity, extracted with chloroform (15ml×3), washed the organic phase with saturated brine, dried over anhydrous magnesium sulfate, evaporated with a rotary evaporator The solvent was removed to obtain a yellow oil, which was subjected to column chromatography (eluent: n-hexane: ethyl acetate = 3:1) to obtain 0.42 g of compound II.

[0031] The preparation of 1-(aminomethyl)-cyclohexylacetic acid hydrochloride I

[0032] Compound 2-aza-spiro[4,...

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Abstract

A process for synthesizing gabapentin hydrochloride includes such steps as Backmann rearrangement reaction of spiro [3,5]-2-nonanone ó¾ to obtain 2-aza-spiro [4,5]-3-decanone ó�, hydrolyzing, and recrystallizing. Its advantages are simple process, low poison of raw material and low cost.

Description

technical field [0001] The present invention belongs to the field of compound synthesis. Specifically relates to a new synthesis method of gabapentin hydrochloride. Background technique [0002] The chemical name of Gabapentin is 1-(aminomethyl)-cyclohexylacetic acid. It is a new generation of antiepileptic drugs. Recent clinical applications have shown that it is very effective in controlling neurogenic disorders including postherpetic neuralgia. sexual pain. It has the advantages of being well tolerated, with transient and mild side effects, and most patients can tolerate gabapentin even when taking high doses of other drugs. [0003] Bibliographical reports gabapentin hydrochloride, the synthetic method of chemical name 1-(aminomethyl)-cyclohexyl acetic acid hydrochloride mainly contains three kinds: the one, Warner Lambertd etc. set out from cyclohexanone and make cyclohexyl through three-step reaction Substituted glutaric anhydride, then through the rearrangement rea...

Claims

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Application Information

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IPC IPC(8): C07C229/28C07C227/22
Inventor 柏旭徐显秀吴劲昌
Owner CHANGCHUN DISCOVERY SCI
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