Morpholine → 3-(2-(4-Morpholinyl)ethoxy)-5-phenylisoxazole
Reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Br[CH2:8][CH2:9][O:10][C:11]1[CH:15]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[O:13][N:12]=1>>[N:1]1([CH2:8][CH2:9][O:10][C:11]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[O:13][N:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1Participants
3
Conditions
- Temperature
- 100 °C
Procedure
Morpholine (871 mg) was added to 3-(2-bromoethoxy)-5-phenylisoxazole (268 mg), and the mixture was stirred at 100° C. for one hour. After ice-cold water (20 ml) was added to the reaction mixture and the resulting mixture was extracted with ether (20 ml×2), the organic layer was dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate) to obtain the title compound (250 mg, 91%) as colorless crystals.