Ammonia → HCID 178511286, compound

HRID 1819471Notes

Reaction equation

HRID 1819471 reaction equation
N.[OH:2][C@@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]#[N:10])[CH2:5][CH2:4]1>CO.[Ni]>[NH2:10][CH2:9][C@@H:6]1[CH2:7][CH2:8][C@H:3]([OH:2])[CH2:4][CH2:5]1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 178511284HCID 178511284, compound

Product 1

HCID 178511286HCID 178511286, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a 2 N solution of NH3 in MeOH (40 mL) in a high pressure autoclave was added cis-4-hydroxy-cyclohexanecarbonitrile (6.6 g, 52.7 mmol) and Raney Ni (1.0 g, 17 mmol, 0.3 equiv.) The mixture was placed under 45 psi H2 and shaken overnight. The pressure was released and the reaction filtered through a pad of Celite. The filter pad was washed with EtOAc and the mixture was concentrated under reduced pressure to provide a yellow oil as cis-4-aminomethyl-cyclohexanol (6.3 5g, 49.1 mmol, 93.2%).

Workup

  1. filtrationthe reaction filtered through a pad of Celite
  2. washThe filter pad was washed with EtOAc
  3. concentrationthe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-971a7d28f6e54eee85eb1791e66e053d
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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