Morpholine → 3-(2-(4-Morpholinyl)ethoxy)-5-phenylisoxazole

HRID 612930Notes

Reaction equation

HRID 612930 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]1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 195964873-(2-Bromoethoxy)-5-phenylisoxazole

Product 1

HCID 195964643-(2-(4-Morpholinyl)ethoxy)-5-phenylisoxazoleYield 91.2%

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.

Workup

  1. extractionthe resulting mixture was extracted with ether (20 ml×2)
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationAfter filtration
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-3a982ba9859643fbbc1c08970370a9ea
Source dataset
uspto-grants-1999_12
Patent number
US06005116

Reaction notes

Loading…