(1-Cyanocyclohexyl)acetic acid → Gabapentin

HRID 974435Notes

Reaction equation

HRID 974435 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].[H][H]>CO.[C].[Rh]>[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 2

HCID 11073797(1-Cyanocyclohexyl)acetic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 3446GabapentinYield 65.1%

Reagents, catalysts & solvents 2

HCID 178503043HCID 178503043, compoundCatalystHCID 887MethanolSolvent

Procedure

A solution of 3 g (1-cyanocyclohexyl)-acetic acid in 10.5 mL methanol is hydrogenated at 10 bar hydrogen pressure and 30° C. in the presence of rhodium-carbon (5%) over a period of five hours. The reaction mixture is filtered and the filtrate evaporated on a rotary evaporator at 30° C. The crystalline residue is stirred with isopropanol and the crystallizate is filtered off with suction and dried to constant weight in a vacuum drying cabinet at 30° C. 2.0 g of the title compound are obtained (65.2% of theory); m.p. 152° C.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customthe filtrate evaporated on a rotary evaporator at 30° C
  3. filtrationthe crystallizate is filtered off with suction
  4. customdried to constant weight in a vacuum
  5. customdrying cabinet at 30° C

Sources & evidence

ORD record
ord-07919c189aa1474ca048abd3b9bb8a87
Source dataset
uspto-grants-1991_11
Patent number
US05068413

Reaction notes

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