Pyridine → 6-(4-Chlorophenyl)-1-phenyl-2-piperidone

HRID 1904614Notes

Reaction equation

HRID 1904614 reaction equation
[NH:1]([CH:8]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)[CH2:9][CH2:10][CH2:11][C:12](O)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.S(Cl)(Cl)=O>C1(C)C=CC=CC=1>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([CH:8]2[N:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:12](=[O:13])[CH2:11][CH2:10][CH2:9]2)=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 145768135-Anilino-5-(4-chlorophenyl)pentanoic acid

Product 1

HCID 145768146-(4-Chlorophenyl)-1-phenyl-2-piperidoneYield 97.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

(2)-(a) A solution of 17.8 g of 5-anilino-5-(4-chlorophenyl)pentanoic acid in a mixed solution of 290 ml of toluene and 13.9 g of pyridine was cooled to -3° C. and stirred. To this solution was added 10 ml solution of 5.1 ml of thionyl chloride in toluene dropwise over 1 hour. After stirring at -3° C. for 1 hour and at room temperature for 1.5 hours, the reaction mixture was poured into ice-water. The toluene layer was washed with diluted hydrochloric acid, a saturated aqueous sodium chloride solution, a saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution, dried and treated with activated charcoal. After removal of charcoal and the solvent, the residual solid was recrystallized from isopropyl ether to give 16.4 g of 6-(4-chlorophenyl)-1-phenyl-2-piperidone as colorless prisms.

Workup

  1. stirringAfter stirring at -3° C. for 1 hour and at room temperature for 1.5 hours
  2. washThe toluene layer was washed with diluted hydrochloric acid
  3. dry with materiala saturated aqueous sodium chloride solution, a saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution, dried
  4. additiontreated with activated charcoal
  5. customAfter removal of charcoal
  6. customthe solvent, the residual solid was recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-6719cdbb382646dab1855e36a32313e8
Source dataset
uspto-grants-1989_06
Patent number
US04839360

Reaction notes

Loading…