Water → 4-Benzylmorpholin-3-one

HRID 1612756Notes

Reaction equation

HRID 1612756 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:15][C:16](OCC)=O.[OH2:21]>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:16][CH2:15][O:11][CH2:10][C:9]1=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 4348BenzylethanolamineHCID 7748Ethyl bromoacetateHCID 24758Sodium hydride

Product 1

HCID 122940874-Benzylmorpholin-3-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

A solution of N-benzyl ethanolamine (60.4 g, 0.40 mol) in toluene (400 ml) was added over a period of 1 hour to a mechanically stirred suspension of sodium hydride (60% dispersion in mineral oil, 17.6 g, 0.44 mol) in toluene (800 ml). The reaction was heated under reflux for 2 hours before being cooled to room temperature and a solution of ethyl bromoacetate (44.4 ml, 0.40 mol) in toluene (600 ml) added over a period of 30 minutes. The reaction was then heated under reflux for 15 hours before being cooled to room temperature and water (1000 ml) added. The aqueous phase was extracted with ethyl acetate (3×200 ml) and the combined organic phases washed with brine (500 ml), dried with sodium sulphate and evaporated in vacuo. The resulting oil was purified by flash column chromatography upon silica gel using ethyl acetate: hexanes: triethylamine (70:28:2) as eluant affording the desired product as a yellow oil, 32 g, M+ found: 191.

Workup

  1. temperatureThe reaction was heated
  2. temperatureunder reflux for 2 hours
  3. temperatureThe reaction was then heated
  4. temperatureunder reflux for 15 hours
  5. temperaturebefore being cooled to room temperature
  6. extractionThe aqueous phase was extracted with ethyl acetate (3×200 ml)
  7. washthe combined organic phases washed with brine (500 ml)
  8. dry with materialdried with sodium sulphate
  9. customevaporated in vacuo
  10. customThe resulting oil was purified by flash column chromatography upon silica gel

Sources & evidence

ORD record
ord-ecd770361ff942fcac9b3e3446f6f08a
Source dataset
uspto-grants-1993_03
Patent number
US05190958

Reaction notes

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