p-Fluoronitrobenzene → 1-(4-Nitrophenyl)piperidin-4-one

HRID 37846

Reaction equation

HRID 37846 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1.C[O-].[Na+].C(=O)([O-])[O-].[K+].[K+].F[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1>>[N+:25]([C:22]1[CH:23]=[CH:24][C:19]([N:2]2[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]2)=[CH:20][CH:21]=1)([O-:27])=[O:26]

Participants

5

Reactant 4

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 30848514-Piperidone hydrochlorideHCID 10942334Sodium Methoxide

Product 1

HCID 38425621-(4-Nitrophenyl)piperidin-4-oneYield 37%

Procedure

Piperidin-4-one hydrochloride was added to a methanolic solution of sodium methoxide (prepared from anhydrous methanol (50 mL) and sodium metal (0.85 g, 37 mmol)) and heated at reflux for 2 h then concentrated to dryness in vacuo. The residue was dissolved in acetonitrile (100 mL), then potassium carbonate (10.22 g, 74 mmol) and 1-fluoro-4-nitro-benzene (3.92 mL, 37 mmol) were added and the mixture was heated at reflux overnight. The solvent was evaporated in vacuo, the residue being washed with water then 50% diethyl ether/petroleum ether and dried in vacuo to afford 1-(4-nitro-phenyl)-piperidin-4-one (3.01 g, 37%) as a yellow solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 h
  3. concentrationthen concentrated to dryness in vacuo
  4. dissolutionThe residue was dissolved in acetonitrile (100 mL)
  5. temperaturethe mixture was heated
  6. temperatureat reflux overnight
  7. customThe solvent was evaporated in vacuo
  8. washthe residue being washed with water
  9. dry with material50% diethyl ether/petroleum ether and dried in vacuo

Sources & evidence

ORD record
ord-49e8b3dab6e44043b8dc93c7ea9a469e
Source dataset
uspto-grants-2013_09
Patent number
US08524705B2

Linked notes

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