Ammonia → Cyclohexanemethylamine, 1-phenyl-

HRID 1107439Notes

Reaction equation

HRID 1107439 reaction equation
[C:1]1([C:7]2([C:13]#[N:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCO.N>C(Cl)Cl.[Rh]>[C:1]1([C:7]2([CH2:13][NH2:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 702EthanolHCID 751481-Phenylcyclohexanecarbonitrile

Product 1

HCID 205110Cyclohexanemethylamine, 1-phenyl-

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture containing 1-phenyl-1-cyclohexane-carbonitrile (5.0 g, 27.0 mmol), 150 ml of EtOH, 35 ml of ammonia and 5% rhodium on alumina (1.0 g) was reacted for 12 hours at 80° C. and 500 psi. The mixture was filtered and the filtrate was concentrated in vacuo to provide an oil. This oil was dissolved in CH2Cl2, washed with brine, dried over Na2SO4, filtered and then concentrated in vacuo.

Workup

  1. customwas reacted for 12 hours at 80° C.
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto provide an oil
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d56e7118374b4e1697b1196970ab8bfe
Source dataset
uspto-grants-2000_05
Patent number
US06060484

Reaction notes

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