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

HRID 56100Notes

Reaction equation

HRID 56100 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CCN(CC)CC.F[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:16]=1[F:24]>CCOC(C)=O>[F:24][C:16]1[CH:17]=[C:18]([N+:21]([O-:23])=[O:22])[CH:19]=[CH:20][C:15]=1[N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 8471TriethylamineHCID 1230531,2-Difluoro-4-nitrobenzene

Product 1

HCID 107043451-(2-Fluoro-4-nitrophenyl)piperidineYield 99.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of piperidine (5.88 g, 69 mmol) and Et3N (6.98 g, 69 mmol) in EtOAc (60 mL) was added 1,2-difluoro-4-nitrobenzene (10.00 g, 63 mmol) dropwise. The mixture was stirred at rt overnight. The resulting mixture was washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo to give the title compound as a yellow solid (14.00 g, 99%).

Workup

  1. washThe resulting mixture was washed with brine
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e03d6bb1801d42d4b779a7b74f77f155
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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