(1-Cyanocyclohexyl)acetic acid → Gabapentin

HRID 1868430Notes

Reaction equation

HRID 1868430 reaction equation
[C:1]([C:3]1([CH2:9][C:10]([OH:12])=[O:11])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)#[N:2]>CO.[Rh].[Pd]>[CH2:6]1[CH2:5][CH2:4][C:3]([CH2:1][NH2:2])([CH2:9][C:10]([OH:12])=[O:11])[CH2:8][CH2:7]1

Participants

5

Reactant 1

HCID 11073797(1-Cyanocyclohexyl)acetic acid

Product 1

HCID 3446Gabapentin

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 23948RhodiumCatalystHCID 887MethanolSolvent

Procedure

In U.S. Pat. Nos. 5,132,451, 5,319,135 & 6,294,690, 1-cyanocyclohexane acetic acid was hydrogenated in methanol at room temperature for 2 hours, using 15% Rhodium on carbon catalyst containing 1% palladium. The mixture was filtered and the filtrate concentrated. Addition of isopropanol and stirring at 0-5 deg for 24 hrs gave gabapentin. In EP Patent no 414262B1,1-cyano cyclohexene acetic acid was hydrogenated on Raney nickel to produce Gabapentin.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated
  3. additionAddition of isopropanol

Sources & evidence

ORD record
ord-8cd7a83d20b744baae789e392aea2c01
Source dataset
uspto-grants-2009_12
Patent number
US07635717B2

Reaction notes

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