Water → 4-Morpholinobenzonitrile

HRID 887191Notes

Reaction equation

HRID 887191 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.O>CS(C)=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][O:13][CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 962WaterHCID 8083MorpholineHCID 145174-Fluorobenzonitrile

Product 1

HCID 3948084-MorpholinobenzonitrileYield 80%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

4-Fluorobenzonitrile (1 g, 8.26 mmol) and morpholine (2.2 mL, 25.2 mmol) were combined in DMSO (25 mL) and heated at 100° C. for 2.5 hours. The mixture was allowed to cool to room temperature, poured into water, and extracted with diethyl ether. The organic extracts were combined, washed with water and brine, dried over Na2SO4, and concentrated under reduced pressure to provide the title compound as a white solid (1.24 g, 80%).

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with diethyl ether
  3. washwashed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e28973f0828142088d9532dd59de08f4
Source dataset
uspto-grants-2012_08
Patent number
US08247413B2

Reaction notes

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