(1-Aminomethyl)-cyclohexaneacetic acid hydrochloride hydrate → Gabapentin hydrochloride

HRID 1087985Notes

Reaction equation

HRID 1087985 reaction equation
O.[ClH:2].[NH2:3][CH2:4][C:5]1([CH2:11][C:12]([OH:14])=[O:13])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1>O>[ClH:2].[NH2:3][CH2:4][C:5]1([CH2:11][C:12]([OH:14])=[O:13])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

3

Reactant 1

HCID 22664988(1-Aminomethyl)-cyclohexaneacetic acid hydrochloride hydrate

Product 1

HCID 6453919Gabapentin hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An ion exchange column is prepared by filling a glass column with 380 mL of Amberlite RIRA-68. The resin is rinsed with a dilute ammonia solution, 140 mL ammonium hydroxide in 3 L water, followed by deionized water to a neutral pH, (about 2 L). A 1 N solution of (1-aminomethyl)-cyclohexaneacetic acid hydrochloride is prepared by dissolving 64.6 g of (1-aminomethyl)-cyclohexaneacetic acid hydrochloride hydrate (4:4:1) in 310 mL of deionized water. This solution is filtered through a filter to remove any insoluble material or extracted with an organic solvent such as dichloromethane.

Workup

  1. customAn ion exchange column is prepared
  2. washThe resin is rinsed with a dilute ammonia solution, 140 mL ammonium hydroxide in 3 L water
  3. filtrationThis solution is filtered through
  4. filtrationa filter
  5. customto remove any insoluble material
  6. extractionextracted with an organic solvent such as dichloromethane

Sources & evidence

ORD record
ord-b9946e0242814478be92897271cc588a
Source dataset
uspto-grants-1990_10
Patent number
US04960931

Reaction notes

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