Methanol → Gabapentin

HRID 330097

Reaction equation

HRID 330097 reaction equation
O.[NH2:2][CH2:3][C:4]1([CH2:10][C:11]([OH:13])=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.CO>CC(O)C>[NH2:2][CH2:3][C:4]1([CH2:10][C:11]([OH:13])=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 887MethanolHCID 14598836Gabapentin monohydrate

Product 1

HCID 3446Gabapentin

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A slurry of 179 Kg of 1-(aminomethyl)-cyclohexaneacetic acid monohydrate and 1266 Kg of anhydrous methanol is heated to 60° C. to give a complete solution. The solution is diluted with 1266 Kg of anhydrous 2-propanol and the solution is cooled to 20° C. to 25° C. for two hours and then is cooled to -8° C. to -10° C. for twenty hours. The resulting slurry is centrifuged and the precipitate is dried in vacuo at 35° C. for forty-eight hours to yield 145 Kg of white, crystalline 1-(aminomethyl)-cyclohexaneacetic acid.

Workup

  1. customto give a complete solution
  2. temperaturethe solution is cooled to 20° C. to 25° C. for two hours
  3. temperatureis cooled to -8° C. to -10° C. for twenty hours
  4. customthe precipitate is dried in vacuo at 35° C. for forty-eight hours

Sources & evidence

ORD record
ord-1c71c6737f7b49f08c364ebdaddb9d8b
Source dataset
uspto-grants-1990_01
Patent number
US04894476

Linked notes

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