Morpholine → 4-Morpholinobenzonitrile

HRID 49830

Reaction equation

HRID 49830 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.[F-].[K+]>CS(C)=O.CCOC(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

6

Reactant 3

HCID 8083MorpholineHCID 145174-FluorobenzonitrileHCID 522689Potassium Fluoride

Product 1

HCID 3948084-MorpholinobenzonitrileYield 60%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A solution of 4-fluorobenzonitrile (1.00 g, 8.26 mmol) and morpholine (0.77 mL, 9.08 mmol) in dimethyl sulfoxide (40 mL) was treated with 37% KF on alumina, and the mixture was heated at 150° C. for 5 h. After cooling, the mixture was diluted with EtOAc and filtered through diatomaceous earth. The filtrate was washed with water (3×), brine (1×), and then dried with magnesium sulfate. The extract was concentrated and the residue was purified by chromatography (SiO2, 20 to 30% EtOAc in hexanes) yielding 930 mg (60%) of the title compound.

Workup

  1. temperatureAfter cooling
  2. filtrationfiltered through diatomaceous earth
  3. washThe filtrate was washed with water (3×), brine (1×)
  4. dry with materialdried with magnesium sulfate
  5. concentrationThe extract was concentrated
  6. customthe residue was purified by chromatography (SiO2, 20 to 30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-c8c5fd3a90484677ba6430f82ed61f7d
Source dataset
uspto-grants-2004_03
Patent number
US06710057B2

Linked notes

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