Morpholine → HCID 15630379, compound

HRID 1109511Notes

Reaction equation

HRID 1109511 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:14][CH:15]([OH:30])[CH2:16][N:17]1[C:21](=[O:22])[C:20]([CH3:23])=[C:19]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[O:18]1>C(O)C>[OH:30][CH:15]([CH2:14][N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)[CH2:16][N:17]1[C:21](=[O:22])[C:20]([CH3:23])=[C:19]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[O:18]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 19020730HCID 19020730, compound

Product 1

HCID 15630379HCID 15630379, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.55 g (17.9 mmoles) of morpholine and 2.46 g (17.9 mmoles) of anhydrous potassium carbonate powder were added to a solution of 4.00 g (14.9 mmoles) of 2-(3-chloro-2-hydroxypropyl)-4-methyl-5-phenyl-3-isoxazolone in 50 ml of ethanol, and the mixture was heated under reflux for 4 hours. At the end of this time, the reaction mixture was cooled by allowing it to stand, and then insoluble materials were removed by filtration. The filtrate was then concentrated by evaporation under reduced pressure, and the residue was purified by column chromatography through silica gel, using ethyl acetate containing 5% by volume methanol as the eluent, to give 4.21 g (yield 83.5%) of the title compound as a colorless syrupy substance.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. temperatureAt the end of this time, the reaction mixture was cooled
  4. custominsoluble materials were removed by filtration
  5. concentrationThe filtrate was then concentrated by evaporation under reduced pressure
  6. customthe residue was purified by column chromatography through silica gel

Sources & evidence

ORD record
ord-179558a47bc544f5bac84e8ee905a38c
Source dataset
uspto-grants-1994_06
Patent number
US05321037

Reaction notes

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