Dimethylformamide → HCID 14576903, compound

HRID 1904622Notes

Reaction equation

HRID 1904622 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:13]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[C:12](=[O:21])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.CN(C)C=O>[C].[Pd].C(O)=O>[F:20][C:17]1[CH:16]=[CH:15][C:14]([N:13]2[CH:8]([C:5]3[CH:4]=[CH:3][CH:2]=[CH:7][CH:6]=3)[CH2:9][CH2:10][CH2:11][C:12]2=[O:21])=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 14576861HCID 14576861, compound

Product 1

HCID 14576903HCID 14576903, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 284Formic AcidSolvent

Procedure

A mixture of 2.32 g of 6-(4-chlorophenyl)-1-(4-fluorophenyl)-2-piperidone, 25 ml of dimethylformamide, 5 ml of formic acid, and 1.0 g of palladium-carbon was refluxed for 6 hours. The catalyst was filtered off, and the filtrate was extracted with ethyl acetate. The ethyl acetate solution was washed with water and an aqueous sodium hydrogen carbonate solution and dried. After removal of the solvent, the residue was recrystallized from a mixture of isopropyl ether and n-hexane to give 1.25 g of 1-(4-fluorophenyl)-6-phenyl-2-piperidone as colorless prisms.

Workup

  1. temperaturewas refluxed for 6 hours
  2. filtrationThe catalyst was filtered off
  3. extractionthe filtrate was extracted with ethyl acetate
  4. washThe ethyl acetate solution was washed with water
  5. dry with materialan aqueous sodium hydrogen carbonate solution and dried
  6. customAfter removal of the solvent
  7. customthe residue was recrystallized from a mixture of isopropyl ether and n-hexane

Sources & evidence

ORD record
ord-2fe8e3c9f0c4496f80b71a3f981b3399
Source dataset
uspto-grants-1989_06
Patent number
US04839360

Reaction notes

Loading…