Water → 4-Phenylcyclohexylamine

HRID 1048141Notes

Reaction equation

HRID 1048141 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][C:10](=[N:13]O)[CH2:9][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[CH2:8][CH2:9][CH:10]([NH2:13])[CH2:11][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 3438824-Phenylcyclohexanone oximeHCID 21226445Aluminium lithium hydride

Product 1

HCID 298974-PhenylcyclohexylamineYield 34.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-phenylcyclohexanone oxime (0.310 g, 1.64 mmol) in THF (3 ml) was added 1M lithium aluminum hydride in THF (3.44 ml, 3.44 mmol), and the reaction was heated to reflux for 4 hours. The reaction was allowed to cool to ambient temperature, and water (0.131 ml), 1M NaOH (0.131 ml) and additional water (0.393 ml) were added, and the reaction was stirred for 30 minutes. The reaction was diluted with EtOAc and filtered. The filtrate was concentrated to yield 100 mg of the title compound (34.8% yield) as a 1:1 mixture of cis and trans isomers.

Workup

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

Sources & evidence

ORD record
ord-cfa52847d1a545f38b12bf45c7dc67b6
Source dataset
uspto-grants-2013_10
Patent number
US08569522B2

Reaction notes

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