Hydrochloric Acid → 4,4-Dimethylcyclohexan-1-amine

HRID 852635Notes

Reaction equation

HRID 852635 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:7][CH2:6][C:5](=[N:8]O)[CH2:4][CH2:3]1.Cl>CCO.[Ni]>[CH3:1][C:2]1([CH3:10])[CH2:7][CH2:6][CH:5]([NH2:8])[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 279448N-(4,4-dimethylcyclohexylidene)hydroxylamine

Product 1

HCID 4210544,4-Dimethylcyclohexan-1-amineYield 89%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

4,4-Dimethylcyclohexanone oxime (D296) (10 g, 71 mmol, 1 equiv) in EtOH (100 ml) was stirred with Raney Ni (1 g, 10% w/w) under an atmosphere of H2 (50 psi) for 4 days. The catalyst was filtered off through a pad of celite and HCl (1M in Et2O, 100 ml, 100 mmol, 1.4 equiv) were added. The precipitate formed was filtered off and dissolved in water. The aqueous phase was washed with Et2O and made strongly basic with KOH pellets then extracted twice with CH2Cl2. The combined organic phases were dried over MgSO4 and concentrated in vacuo to give 4,4-dimethylcyclohexanamine (F83) (8 g, 89%) as a clear oil which was used in the next step without further purification.

Workup

  1. additionwere added
  2. customThe precipitate formed
  3. filtrationwas filtered off
  4. dissolutiondissolved in water
  5. washThe aqueous phase was washed with Et2O
  6. extractionthen extracted twice with CH2Cl2
  7. dry with materialThe combined organic phases were dried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-27254c4c3d6744e58c7489d55602d1e4
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

Loading…