Azane;hydrate → 6-(4-Cyanophenyl)-1-phenyl-2-piperidone

HRID 1904623Notes

Reaction equation

HRID 1904623 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:12](=[O:20])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[Cu](C#N)[C:22]#[N:23].O.N>N1C=CC=CC=1>[C:22]([C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:12](=[O:20])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1)#[N:23]

Participants

5

Reactant 3

HCID 12896473Azane;hydrateHCID 145768146-(4-Chlorophenyl)-1-phenyl-2-piperidoneHCID 178418260HCID 178418260, compound

Product 1

HCID 145769046-(4-Cyanophenyl)-1-phenyl-2-piperidoneYield 47%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
240 °C

Procedure

To 8.55 g of 6-(4-chlorophenyl)-1-phenyl-2-piperidone were added 5.58 g of copper cyanide and 14 ml of pyridine, and the mixture was heated with stirring at 240° C. for 19 hours. The mixture was treated with diluted ammonia water, and then extracted with ethyl acetate. The extracts were washed with water, dried and treated with activated charcoal. After removal of charcoal and the solvent, the residue was purified by silica gel column chromatography (solvent; ethyl acetate:n-hexane=1:1 to 3), and recrystallized from a mixture of ethyl acetate and isopropyl ether to give 3.48 g of 6-(4-cyanophenyl)-1-phenyl-2-piperidone as pale yellow prisms.

Workup

  1. temperaturethe mixture was heated
  2. extractionextracted with ethyl acetate
  3. washThe extracts were washed with water
  4. customdried
  5. additiontreated with activated charcoal
  6. customAfter removal of charcoal
  7. customthe solvent, the residue was purified by silica gel column chromatography (solvent; ethyl acetate:n-hexane=1:1 to 3)
  8. customrecrystallized from a mixture of ethyl acetate and isopropyl ether

Sources & evidence

ORD record
ord-055885ae56e34506ab05b1f22e32c6cc
Source dataset
uspto-grants-1989_06
Patent number
US04839360

Reaction notes

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