Triethylamine → 1-(4-Nitrophenyl)piperidin-4-one

HRID 450056Notes

Reaction equation

HRID 450056 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1.C(N(CC)CC)C.C(=O)([O-])[O-].[K+].[K+].F[C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1>C(#N)C.O>[N+:29]([C:26]1[CH:27]=[CH:28][C:23]([N:2]2[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]2)=[CH:24][CH:25]=1)([O-:31])=[O:30]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 30848514-Piperidone hydrochloride

Product 1

HCID 38425621-(4-Nitrophenyl)piperidin-4-oneYield 38.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To 4-piperidone hydrochloride (2.17 g, 16.0 mmol) in acetonitrile (20 ml) was added triethylamine (3.9 ml) and potassium carbonate (2.9 g, 21.0 mmol). After stirring for 20 min at room temperature, 1-fluoro-4-nitrobenzene (1 g, 7.09 mmol) was added and the reaction mixture was heated to reflux for 12 hr. The reaction mixture was then cooled and filtered and the filtrate concentrated under reduced pressure to give a residue. The residue was dissolved in water, extracted with ethyl acetate, dried and evaporated to give 1-(4-nitro-phenyl)-piperidin-4-one (0.6 g, 38%).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 12 hr
  3. temperatureThe reaction mixture was then cooled
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customto give a residue
  7. extractionextracted with ethyl acetate
  8. customdried
  9. customevaporated

Sources & evidence

ORD record
ord-31cf5857769f456e935d8de674d0059f
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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