Piperidine → 4-piperidin-1-ylbenzonitrile

HRID 2244280Notes

Reaction equation

HRID 2244280 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[NH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O.O>[N:10]1([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

6

Reactant 3

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 145174-Fluorobenzonitrile

Product 1

HCID 7667714-piperidin-1-ylbenzonitrileYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-fluorobenzonitrile (1 g, 8.26 mmol), piperidine (0.90 mL, 9.08 mmol) and potassium carbonate (2.28 g, 16.51 mmol) in dry 1-methyl-2-pyrrolidinone (10 mL) was stirred at 120° C. under nitrogen for 20 hours. The cooled reaction mixture was then diluted with water (100 mL) and extracted with ethyl acetate (100 mL). The organic extract was washed with water (100 mL) and brine (100 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo to afford an orange oil. Purification by flash chromatography using a solvent gradient of 1 to 7% ethyl acetate in hexane gave an orange oil that was crystallized from hexane to afford the title compound (1.41 g, 92%) as an orange crystalline solid, m.p. 54° C.

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted with ethyl acetate (100 mL)
  3. extractionThe organic extract
  4. washwas washed with water (100 mL) and brine (100 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto afford an orange oil
  8. customPurification by flash chromatography
  9. customgave an orange oil that
  10. customwas crystallized from hexane

Sources & evidence

ORD record
ord-e42f5c9287e24e549b5f70e9d8945dce
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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