Morpholine → Ethanone, 2-(4-morpholinyl)-1-phenyl-

HRID 1029909Notes

Reaction equation

HRID 1029909 reaction equation
F[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O>[N:11]1([CH2:2][C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:4])[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 99472-Fluoro-1-phenylethan-1-oneHCID 11430Potassium Carbonate

Product 1

HCID 409383Ethanone, 2-(4-morpholinyl)-1-phenyl-

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-fluoroacetophenone (19.9 g), morpholine (21 cc) and potassium carbonate (27.6 g) in dimethyl sulphoxide (32 cc) is heated at 110° C. for 30 hours. The reaction mixture is diluted with water (100 cc) and extracted with ethyl acetate (4×100 cc); the organic solution is washed with distilled water (100 cc), dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a silica gel column (0.04-0.063 mm, diameter 9 cm, height 40 cm), eluting with a mixture of cyclohexane and ethyl acetate (80/20 by volume) and collecting 250 cc fractions. Fraction 24 to 44 are combined and concentrated to dryness under reduced pressure (2.7 kPa). 2-(4-Morpholinyl)acetophenone (4.72 g) is obtained which is used as such for the subsequent syntheses.

Workup

  1. extractionextracted with ethyl acetate (4×100 cc)
  2. washthe organic solution is washed with distilled water (100 cc)
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  5. customThe residue is chromatographed on a silica gel column (0.04-0.063 mm, diameter 9 cm, height 40 cm)
  6. washeluting with a mixture of cyclohexane and ethyl acetate (80/20 by volume)
  7. customcollecting 250 cc fractions
  8. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-1f0fbc109ffd44a294702c9d858a21e1
Source dataset
uspto-grants-1992_04
Patent number
US05102667

Reaction notes

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