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

HRID 1109520Notes

Reaction equation

HRID 1109520 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[O:7]1[CH2:22][CH:8]1[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>C(O)C>[OH:7][CH:8]([CH2:22][N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)[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

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

17.6 g of morpholine were added to a solution of 40.0 g of 3-(2,3-epoxypropoxy)-5-phenylisoxazole (prepared as described in Preparation 4) in 400 ml of ethanol, and the mixture was heated under reflux for 5 hours. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure, and the resulting solid residue was recrystallized from ethyl acetate, to give 50.0 g (yield 89.2%) of the title compound as colorless columnar crystals, melting at 123°-124° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hours
  3. concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
  4. customthe resulting solid residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-17902df026a74c3ca349959286a71719
Source dataset
uspto-grants-1994_06
Patent number
US05321037

Reaction notes

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