Morpholine → 3-(2-Hydroxy-3-morpholinopropoxy)-5-phenylisoxazole

HRID 1587347Notes

Reaction equation

HRID 1587347 reaction equation
[O:1]1[CH2:16][CH:2]1[CH2:3][O:4][C:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:7][N:6]=1.[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>C(O)C>[OH:1][CH:2]([CH2:16][N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)[CH2:3][O:4][C:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:7][N:6]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 148844763-(2,3-Epoxypropoxy)-5-phenylisoxazole

Product 1

HCID 146520273-(2-Hydroxy-3-morpholinopropoxy)-5-phenylisoxazoleYield 89.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 40.0 g of 3-(2,3-epoxypropoxy)-5-phenylisoxazole dissolved in ethanol (400 ml) was added 17.6 g of morpholine and the mixture was refluxed by heating for 5 hours, followed by concentration under reduced pressure. The resulting solid was recrystallized from ethyl acetate to afford 50.0 g of the title compound with melting point 123°-124° C. as colorless columns.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureby heating for 5 hours
  3. concentrationfollowed by concentration under reduced pressure
  4. customThe resulting solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-b42ef535d65f451b866f0b52538c95e3
Source dataset
uspto-grants-1993_06
Patent number
US05217970

Reaction notes

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