Toluene → 1-Benzyl-4-((4-fluorophenyl)amino)piperidine-4-carbonitrile

HRID 1683041Notes

Reaction equation

HRID 1683041 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=1.C1(C)C=CC=CC=1.CC(C)(O)[C:32]#[N:33]>O>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([NH:22][C:19]2[CH:20]=[CH:21][C:16]([F:15])=[CH:17][CH:18]=2)([C:32]#[N:33])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 6406Acetone CyanohydrinHCID 97314-FluoroanilineHCID 192201-Benzyl-4-piperidone

Product 1

HCID 30172221-Benzyl-4-((4-fluorophenyl)amino)piperidine-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Combine 1-benzyl-4-oxo-piperidine (100 mmol), 4-fluorophenylamine (110 mmol), and toluene (300 mL). Heat at reflux for 3 h with azeotropic removal of water. Cool to 50° C. Add acetone cyanohydrin (277 mmol). Slowly distill away the acetone. Concentrate the solvent in vacuo to obtain a residue. Chromatograph on silica gel to obtain the title compound.

Workup

  1. temperatureHeat
  2. distillationSlowly distill away the acetone
  3. concentrationConcentrate the solvent in vacuo
  4. customto obtain a residue

Sources & evidence

ORD record
ord-4b92566e4866453db8ef99d28d7d168c
Source dataset
uspto-grants-1997_06
Patent number
US05635510

Reaction notes

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