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

HRID 1612464Notes

Reaction equation

HRID 1612464 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:7][CH2:6][C:5](=[N:8]O)[CH2:4][CH2:3]1.Cl>C(O)C.[Ni].CCOCC>[CH3:1][C:2]1([CH3:10])[CH2:7][CH2:6][CH:5]([NH2:8])[CH2:4][CH2:3]1

Participants

6

Reactant 2

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

Product 1

HCID 4210544,4-Dimethylcyclohexan-1-amine

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 4,4-dimethylcyclohexanone oxime (D52) (10 g) in ethanol (100 ml) was hydrogenated over Raney nickel at 50 psi for 3 days. 1M HCl in ether (100 ml) was added and the solvent removed to afford the amine as the hydrochloride salt. The title compound (D53) was liberated prior to use by dissolving in water and making strongly basic (KOH pallets), extracting with DCM (2×), drying with (Na2SO4) and evaporating the solvent carefully.

Workup

  1. customthe solvent removed

Sources & evidence

ORD record
ord-dee4a3e05d154759bdbba70ff919ce5e
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

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