Piperidine → Piperidine, 1-(4-nitrophenyl)-

HRID 1665636Notes

Reaction equation

HRID 1665636 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.F[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1>CS(C)=O.O>[N+:14]([C:11]1[CH:12]=[CH:13][C:8]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:9][CH:10]=1)([O-:16])=[O:15]

Participants

5

Reactant 2

HCID 8082PiperidineHCID 9590p-Fluoronitrobenzene

Product 1

HCID 81049Piperidine, 1-(4-nitrophenyl)-Yield 533.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Piperidine (362 mg, 0.2 mmol) was added to a solution of 1-fluoro-4-nitro-benzene (200 mg, 1.4 mmol) in DMSO (10 mL) and the mixture was stirred at 80° C. for 20 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated to afford 220 mg (75%) of 1-(4-nitro-phenyl)-piperidine.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine solution
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-67afc154e5e346ec8477de2d794ad9fe
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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