Acetone → Gabapentin hydrochloride

HRID 1535026Notes

Reaction equation

HRID 1535026 reaction equation
[CH2:1]1[C:5]2([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)[CH2:4][C:3](=[O:11])[NH:2]1.[ClH:12].CC(C)=[O:15]>O>[ClH:12].[NH2:2][CH2:1][C:5]1([CH2:4][C:3]([OH:11])=[O:15])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 474572-Azaspiro(4.5)decan-3-one

Product 1

HCID 6453919Gabapentin hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

89 g (0.581 mole) 2-Aza-spiro[4,5]decan-3-one are stirred under reflux for 4 hours with semiconcentrated hydrochloric acid. The reaction mixture is cooled to ambient temperature, diluted with water and extracted with methylene chloride for the removal of the starting material. The aqueous phase is evaporated to dryness in a vacuum and the residue obtained is mixed with acetone. Upon standing, 79.85 g, 1-aminomethyl-1-cyclohexaneacetic acid hydrochloride (64.7% of theory) crystallize out; content 99%; m.p. 123° to 127° C.

Workup

  1. extractionextracted with methylene chloride for the removal of the starting material
  2. customThe aqueous phase is evaporated to dryness in a vacuum
  3. customthe residue obtained
  4. custom79.85 g, 1-aminomethyl-1-cyclohexaneacetic acid hydrochloride (64.7% of theory) crystallize out

Sources & evidence

ORD record
ord-54d29f89f6a04cec8eedcd6f6e22ab29
Source dataset
uspto-grants-1992_02
Patent number
US05091567

Reaction notes

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