HCID 10219854, compound → Gabapentin

HRID 1884594Notes

Reaction equation

HRID 1884594 reaction equation
[N+:1]([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-])=O>CO.[Pd]>[NH2:1][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

4

Reactant 1

HCID 10219854HCID 10219854, compound

Product 1

HCID 3446GabapentinYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2.01 g (0.01 mol) of 1-(nitromethyl)-cyclohexyl-acetic acid in 50 ml of methanol is hydrogenated in the presence of 0.2 g of palladium oil activated carbon at atmospheric pressure. The catalyst is filtered off and the filtrate is concentrated to 10 ml. 20 ml of tetrahydrofuran is added to the residue and the precipitated crystals were filtered off and dried to yield 1.3 g (80%) of the title compound. Mp: 164-169° C.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated to 10 ml
  3. addition20 ml of tetrahydrofuran is added to the residue
  4. filtrationthe precipitated crystals were filtered off
  5. customdried

Sources & evidence

ORD record
ord-c38a6fab258348be8b68010a215fc3d6
Source dataset
uspto-grants-2004_07
Patent number
US06765114B1

Reaction notes

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