methyl 4-(N-benzylamino)-1-methyl-1-cyclohexanecarboxylate → Methyl 4-amino-1-methylcyclohexane-1-carboxylate

HRID 2225483Notes

Reaction equation

HRID 2225483 reaction equation
C([NH:8][CH:9]1[CH2:14][CH2:13][C:12]([CH3:19])([C:15]([O:17][CH3:18])=[O:16])[CH2:11][CH2:10]1)C1C=CC=CC=1.[H][H]>CO.[C].[Pd]>[NH2:8][CH:9]1[CH2:10][CH2:11][C:12]([CH3:19])([C:15]([O:17][CH3:18])=[O:16])[CH2:13][CH2:14]1

Participants

5

Reactant 2

HCID 19004646methyl 4-(N-benzylamino)-1-methyl-1-cyclohexanecarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 19004747Methyl 4-amino-1-methylcyclohexane-1-carboxylateYield 68.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

0.2 g of 10% palladium-carbon was added to a solution of 3.1 g of methyl 4-(N-benzylamino)-1-methyl-1-cyclohexanecarboxylate (Example 15) in 200 ml of methanol. The solution was reacted at room temperature under normal-pressure hydrogen gas. The reaction was stopped after 20 hours, the catalyst was filtered out, and the solvent was removed in vacuo from the filtrate. As a result, 1.4 g of methyl 4-amino-1-methyl-1-cyclohexanecarboxylate was obtained as a pale yellow oil, which had the following physiochemical properties:

Workup

  1. filtrationthe catalyst was filtered out
  2. customthe solvent was removed in vacuo from the filtrate

Sources & evidence

ORD record
ord-37c5bdde4edf4dc9b06b67226728faf9
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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