Morpholine → 4-Morpholinobenzonitrile

HRID 1408154Notes

Reaction equation

HRID 1408154 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>CS(C)=O.O>[O:13]1[CH2:14][CH2:15][N:10]([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)[CH2:11][CH2:12]1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 145174-Fluorobenzonitrile

Product 1

HCID 3948084-MorpholinobenzonitrileYield 79.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

Into a 50-mL 3-necked round-bottom flask, was placed a solution of 4-fluorobenzonitrile (500 mg, 4.13 mmol, 1.00 equiv) in DMSO (5 mL), and morpholine (1070 mg, 12.30 mmol, 3.00 equiv). The resulting solution was stirred for 4 h at 120° C. in an oil bath. The resulting solution was diluted with 100 mL of H2O. The solids were collected by filtration. The product was obtained as 617 mg (79%) of a yellow solid.

Workup

  1. customInto a 50-mL 3-necked round-bottom flask, was placed
  2. filtrationThe solids were collected by filtration

Sources & evidence

ORD record
ord-6d65bbe9a86a4c21ac8636a8153225d9
Source dataset
uspto-grants-2014_12
Patent number
US08916569B2

Reaction notes

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