Potassium Carbonate → 1-(2-Fluoro-4-nitrophenyl)piperidin-4-one

HRID 895124Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[F:14][C:15]1[CH:16]=[C:17]([N+:22]([O-:24])=[O:23])[CH:18]=[CH:19][C:20]=1F>CN(C=O)C>[F:14][C:15]1[CH:16]=[C:17]([N+:22]([O-:24])=[O:23])[CH:18]=[CH:19][C:20]=1[N:1]1[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 90 °C

Procedure

To a stirred solution of 4-piperidinone (9.7 g, 63 mmol) and dry potassium carbonate (21.6 g, 157 mmol) in DMF (30 ml) was added 3,4-difluoro nitrobenzene (10 g, 63 mmol) and reaction mixture was heated to 90° C. for 3 h. The reaction mixture was poured into ice-water arid extracted with ethyl acetate (100 ml×2). Combined organic layer was washed with water followed by brine and dried over sodium sulfate. Evaporation of volatiles and purification of the resulting residue by silica gel column chromatography (ethyl acetate/pet. ether, 1:4) yielded the title compound (7 g, 50%).

Workup

extractionextracted with ethyl acetate (100 ml×2)
washCombined organic layer was washed with water
dry with materialdried over sodium sulfate
customEvaporation of volatiles and purification of the resulting residue by silica gel column chromatography (ethyl acetate/pet. ether, 1:4)

Sources & evidence

ORD record: ord-27f45f036ce040d89472ebef5a934e0e
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06914058B2

Reaction notes

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