Ethyl Acetate → 4-Phenyl-1-(4-cyanophenyl)piperidine

HRID 1249976Notes

Reaction equation

HRID 1249976 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.F[C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN1CCCCC1=O>[C:1]1([CH:7]2[CH2:8][CH2:9][N:10]([C:14]3[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=3)[CH2:11][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 145174-FluorobenzonitrileHCID 698734-Phenylpiperidine

Product 1

HCID 180010564-Phenyl-1-(4-cyanophenyl)piperidineYield 48.7%

Reagents, catalysts & solvents 1

HCID 13603N-Methyl-2-piperidoneSolvent

Conditions

Temperature
120 °C

Procedure

4-Phenylpiperidine (0. 5 g), p-fluorobenzonitrile (0.37 g) and potassium carbonate (0.78 g) are dissolved in N-methylpiperidone (5 ml), and the mixture is stirred at 120° C. for five hours. To the reaction solution is added ethyl acetate (50 ml), and the mixture is washed with water, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. To the resulting residue is added methanol, and the insoluble crystals are collected by filtration, dried under reduced pressure to give 4-phenyl-1-(4-cyanophenyl)piperidine (0.39 g) as white needles.

Workup

  1. washthe mixture is washed with water
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. additionTo the resulting residue is added methanol
  6. filtrationthe insoluble crystals are collected by filtration
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-409f65a68e0e4f41bbdabf5f34dcaecd
Source dataset
uspto-grants-2002_01
Patent number
US06335327B1

Reaction notes

Loading…