Hydrochloric Acid → HCID 69205829, compound

HRID 2118143Notes

Reaction equation

[ClH:1].NCC1(CC(O)=O)CCCC1.[C:13]1([CH2:22][C:23]([OH:25])=[O:24])([CH2:18][C:19]([NH2:21])=[O:20])[CH2:17][CH2:16][CH2:15][CH2:14]1.Cl>>[ClH:1].[C:13]1([CH2:22][C:23]([OH:25])=[O:24])([CH2:18][C:19]([NH2:21])=[O:20])[CH2:14][CH2:15][CH2:16][CH2:17]1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 45010122-(1-(2-Amino-2-oxoethyl)cyclopentyl)acetic acid

HCID 2035620463562-09-4

Product 1

HCID 69205829HCID 69205829, compoundYield 80%

Procedure

U.S. Pat. Nos. 4,024,175 and 4,087,544 disclosed that 1-aminomethyl-1-cyclopentane-acetic acid hydrochloride can be prepared by treating 1,1-cyclopentane-diacetic acid monoamide with NaOH/NaBrO followed by HCl. 1,1-cyclopentane-diacetic acid monoamide hydrochloride was obtained by passing the gabapentin HCl salt through an anion exchange column. However, no yield and purity was reported in these patents. Following similar procedures, except with a cation exchange resin for the last step, WO 02/34709 disclosed a method for the preparation of gabapentin with as much as 80% yield. However, the purity of the product again was not disclosed. These methods require a large amount of solvents for the ion exchange process.

Workup

customcan be prepared

Sources & evidence

ORD record: ord-6e5a115380aa471194fc3a3d8b891a1c
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07442834B2

Reaction notes

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