(1-Phenyl-cyclohexyl)-carbamic acid benzyl ester → 1-Phenylcyclohexylamine

HRID 2235199Notes

Reaction equation

HRID 2235199 reaction equation
C(OC(=O)[NH:10][C:11]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)C1C=CC=CC=1>CO.[Pd]>[C:17]1([C:11]2([NH2:10])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 1

HCID 59299316(1-Phenyl-cyclohexyl)-carbamic acid benzyl ester

Product 1

HCID 318621-PhenylcyclohexylamineYield 90.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Dissolve (1-phenyl-cyclohexyl)-carbamic acid benzyl ester (Preparation 27) (2.87 g, 9.26 mmol) in MeOH (100 mL). Exchange air with nitrogen for three times and then add Pd—C (0.5 g, 10%). Exchange the nitrogen with H2 for three times. Stir the reaction mixture under H2 for over night then remove the Pd—C by filtration. Remove the solvent under reduced pressure to give 1.468 g (90%) of the crude title compound as a colorless oil.

Workup

  1. customthen remove the Pd—C
  2. filtrationby filtration
  3. customRemove the solvent under reduced pressure

Sources & evidence

ORD record
ord-658ad1920c5349a7aedaee767557cf7c
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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