Hydrochloric Acid → 4-Phenylcyclohexan-1-amine--hydrogen chloride (1/1)

HRID 890371

Reaction equation

HRID 890371 reaction equation
O[N:2]=[C:3]1[CH2:8][CH2:7][CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][CH2:4]1.[ClH:15]>[Ni].C(O)C>[ClH:15].[C:9]1([CH:6]2[CH2:5][CH2:4][CH:3]([NH2:2])[CH2:8][CH2:7]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 3438824-Phenylcyclohexanone oxime

Product 1

HCID 2012814-Phenylcyclohexan-1-amine--hydrogen chloride (1/1)Yield 100%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-(hydroxyimino)-4-phenylcyclohexane (17.4 mmol) and Raney Nickel (300 mg) in ethanol was hydrogenated (90 psi) at 50° C. for 40 hours. The mixture was filtered through a pad of Celite, washed with MeOH, and concentrated. The residue was dissolved in MeOH, treated with HCl (4 N in dioxane, 20 mmol), and concentrated to give 4-phenylcyclohexylamine hydrochloride (100%).

Workup

  1. customat 50° C.
  2. customfor 40 hours
  3. filtrationThe mixture was filtered through a pad of Celite
  4. washwashed with MeOH
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in MeOH
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-dce09784419a497ca6dc16664a00ebd5
Source dataset
uspto-grants-2006_02
Patent number
US06995269B2

Linked notes

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