Piperidine → 1-(5-Fluoro-2-nitrophenyl)piperidine

HRID 32893

Reaction equation

HRID 32893 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>CCO>[F:8][C:6]1[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[C:2]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:7]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 679672,4-Difluoronitrobenzene

Product 1

HCID 532567081-(5-Fluoro-2-nitrophenyl)piperidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2,4-difluoronitrobenzene (2.09 g, 13.1 mmol) in EtOH (10 mL) at ambient temperature was added piperidine (3.35 g, 39.4 mmol) dropwise. The reaction was allowed to stir overnight and concentrated in vacuo. The residue was dissolved in EtOAc (100 mL), washed with water (2×100 mL), dried (Na2SO4) and concentrated in vacuo. Purification by silica gel column chromatography afforded 1.10 (37%) of the title compound as an oil. Mass spectrum (ESI, m/z): Calcd. for C11H13FN2O2, 225.1 (M+H), found 225.1.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in EtOAc (100 mL)
  3. washwashed with water (2×100 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel column chromatography

Sources & evidence

ORD record
ord-73ecc3b717224c47a915a4cc25aca307
Source dataset
uspto-grants-2008_09
Patent number
US07427683B2

Linked notes

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