Water → 4-Morpholinobenzonitrile

HRID 2056810Notes

Reaction equation

HRID 2056810 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-6be19ac120134211a49c7be712a4975b
Source dataset
uspto-grants-2008_02
Patent number
US07335678B2

Reaction notes

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