Piperidine → 1-(2-Fluoro-4-nitrophenyl)piperidine

HRID 880484Notes

Reaction equation

HRID 880484 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[F:7][C:8]1[CH:9]=[C:10]([N+:15]([O-:17])=[O:16])[CH:11]=[CH:12][C:13]=1F.C(N(C(C)C)CC)(C)C>C(#N)C>[F:7][C:8]1[CH:9]=[C:10]([N+:15]([O-:17])=[O:16])[CH:11]=[CH:12][C:13]=1[N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 81531DiisopropylethylamineHCID 1230531,2-Difluoro-4-nitrobenzene

Product 1

HCID 107043451-(2-Fluoro-4-nitrophenyl)piperidineYield 92.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Piperidine (0.80 g, 9.42 mmol) was added to a solution of 3,4-difluoro-nitro benzene (1.0 g, 6.28 mmol) in acetonitrile (15 mL) and diisopropyl ethylamine (1.62 g, 12.57 mmol) and the mixture was refluxed for 3 h. The acetonitrile was removed in vacuo and the residue was diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over anhydrous sodium sulphate and concentrated in vacuo to afford 1-(2-fluoro-4-nitro-phenyl)piperidine (1.3 g, 92%) as a yellow liquid.

Workup

  1. temperaturethe mixture was refluxed for 3 h
  2. customThe acetonitrile was removed in vacuo
  3. additionthe residue was diluted with water
  4. extractionextracted with ethyl acetate
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7e425c5665d7458a8ebddabc6ccd6988
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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