p-Toluenesulfonic acid → 6-(4-Chlorophenyl)-1-phenyl-2-piperidone

HRID 1904617Notes

Reaction equation

HRID 1904617 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:14][C:12](=O)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:12](=[O:14])[CH2:11][CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6115AnilineHCID 138480605-(4-Chlorophenyl)-delta-valerolactone

Product 1

HCID 145768146-(4-Chlorophenyl)-1-phenyl-2-piperidoneYield 22.1%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 200 mg of 5-(4-chlorophenyl)-δ-valerolactone, 0.5 g of aniline, 20 mg of p-toluenesulfonic acid and 10 ml of xylene was refluxed for 6 hours. After removal of solvent, the residue was extracted with ethyl acetate. The extract was washed with diluted hydrochloric acid and a saturated aqueous sodium chloride solution and dried. After removal of the solvent, the residue was purified, by silica gel thin layer chromatography (solvent; chloroform:methanol=10:1) to give 60 mg of 6-(4-chlorophenyl)-1-phenyl-2-piperidone.

Workup

  1. temperaturewas refluxed for 6 hours
  2. customAfter removal of solvent
  3. extractionthe residue was extracted with ethyl acetate
  4. washThe extract was washed with diluted hydrochloric acid
  5. dry with materiala saturated aqueous sodium chloride solution and dried
  6. customAfter removal of the solvent
  7. customthe residue was purified, by silica gel thin layer chromatography (solvent; chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-7bb6848790504811ab16e011c0c3e465
Source dataset
uspto-grants-1989_06
Patent number
US04839360

Reaction notes

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