Morpholine → 4-Morpholinobenzonitrile

HRID 1883193Notes

Reaction equation

HRID 1883193 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][O:13][CH2:12][CH2:11]1>CC#N>[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][O:13][CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 145174-Fluorobenzonitrile

Product 1

HCID 3948084-MorpholinobenzonitrileYield 65.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
82 °C

Procedure

Under nitrogen atmosphere, to a solution of 4-fluorobenzonitrile (24.9 g) in CH3CN (500 mL) was added morpholine (53.8 g), and the mixture was stirred at 82° C. for 50 hours. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column (hexane/ethyl acetate=10/1→4/1) to give 4-morpholin-4-yl-benzonitrile (25.3 g, 65%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by silica gel column (hexane/ethyl acetate=10/1→4/1)

Sources & evidence

ORD record
ord-539cc28bb2aa4d87927abd65ae448381
Source dataset
uspto-grants-2004_07
Patent number
US06759429B2

Reaction notes

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