Potassium Cyanide → 3-Oxo-1-phenylcyclohexanecarbonitrile

HRID 1178854Notes

Reaction equation

HRID 1178854 reaction equation
[C:1]1([C:7]2[CH2:12][CH2:11][CH2:10][C:9](=[O:13])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C-]#N.[K+].Cl.[CH3:18][N:19](C)C.C(=O)(O)[O-].[Na+]>O.CN(C=O)C>[O:13]=[C:9]1[CH2:10][CH2:11][CH2:12][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:18]#[N:19])[CH2:8]1

Participants

7

Reactant 4

HCID 9032Potassium CyanideHCID 825672-Cyclohexen-1-one, 3-phenyl-HCID 516892Sodium BicarbonateHCID 10313079Trimethylamine Hydrochloride

Product 1

HCID 123391223-Oxo-1-phenylcyclohexanecarbonitrileYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
93 °C

Procedure

A mixture of 3-phenylcyclohex-2-enone (14.3 mmol), potassium cyanide (1.92 g) and trimethylamine hydrochloride (2.06 g, 21.5 mmol) in H2O (10 mL) and DMF (57 mL) was heated at 93° C. for 6 hr. After cooling down to room temperature, saturated sodium bicarbonate was added and the organic layer was separated. The aqueous layer was extracted with diethyl ether 3 times. The combined organic layers were washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated under vacuum to get 2.62 g of the crude 3-oxo-1-phenylcyclohexanecarbonitrile which was directly taken to the next step without further purification.

Workup

  1. temperatureAfter cooling down to room temperature
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was extracted with diethyl ether 3 times
  4. washThe combined organic layers were washed with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-403b3d06f5c44670bd03b6751b87104e
Source dataset
uspto-grants-2007_10
Patent number
US07276631B2

Reaction notes

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