Water → 3-Phenylcyclohexan-1-amine

HRID 1021520Notes

Reaction equation

HRID 1021520 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][CH2:10][C:9](=[N:13]O)[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1.CCOC(C)=O>[C:1]1([CH:7]2[CH2:12][CH2:11][CH2:10][CH:9]([NH2:13])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 866532373-Phenylcyclohexanone oxime

Product 1

HCID 30281283-Phenylcyclohexan-1-amineYield 74%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-phenylcyclohexanone oxime (0.060 g, 0.32 mmol) in THF (2 ml) was added 1M lithium aluminum hydride in THF (0.67 ml, 0.67 mmol), and the reaction was heated to reflux for 3 hours. The reaction was cooled to ambient temperature and water (0.0254 ml), 1M sodium hydroxide (0.0254 ml), and additional water (0.0762 ml) were added sequentially, and the reaction was stirred for 15 minutes. The reaction was diluted with EtOAc and filtered. The filtrate was concentrated to yield 41 mg of the title compound (74% yield).

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 3 hours
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-c3d811e15b784873a81460d509f7ddd4
Source dataset
uspto-grants-2014_05
Patent number
US08716498B2

Reaction notes

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