Potassium Carbonate → 1-(2,6-Difluoro-4-nitrophenyl)piperidin-4-one

HRID 895129Notes

Reaction equation

HRID 895129 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH:7]1[CH2:12][CH2:11][C:10](=[O:13])[CH2:9][CH2:8]1.[F:14][C:15]1[CH:16]=[C:17]([N+:23]([O-:25])=[O:24])[CH:18]=[C:19]([F:22])[C:20]=1F>CN(C=O)C>[F:14][C:15]1[CH:16]=[C:17]([N+:23]([O-:25])=[O:24])[CH:18]=[C:19]([F:22])[C:20]=1[N:7]1[CH2:12][CH2:11][C:10](=[O:13])[CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 337214-PiperidoneHCID 27827931,2,3-Trifluoro-5-nitrobenzene

Product 1

HCID 218781831-(2,6-Difluoro-4-nitrophenyl)piperidin-4-oneYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of anhydrous potassium carbonate (11.80 g, 85.90 mmol) in DMF (30 ml) was added a solution of 4-piperidinone (7.20 g, 47.2 mmol) in DMF (5 ml) followed by the addition of 3,4,5-trifluoronitrobenzene (7.00 g, 42.8 mmol) and stirred at room temperature for 3 h. The reaction mixture was poured onto ice water and the resulting solid was filtered off. Drying the solid under vacuum yielded the title compound as yellow powder (4.50 g, 45%).

Workup

  1. additionThe reaction mixture was poured onto ice water
  2. filtrationthe resulting solid was filtered off
  3. customDrying the solid under vacuum

Sources & evidence

ORD record
ord-6d5874ebc4a6471094d3808d47ac4ba1
Source dataset
uspto-grants-2005_07
Patent number
US06914058B2

Reaction notes

Loading…