Water → Ethyl 2-(3,5-dimethylmorpholino)acetate

HRID 508699Notes

Reaction equation

HRID 508699 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].[CH3:14][CH:15]1[CH2:20][O:19][CH2:18][CH:17]([CH3:21])[NH:16]1.O>C(#N)C>[CH3:14][CH:15]1[N:16]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:17]([CH3:21])[CH2:18][O:19][CH2:20]1

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 88623,5-DimethylmorpholineHCID 11430Potassium Carbonate

Product 1

HCID 86703011Ethyl 2-(3,5-dimethylmorpholino)acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

Potassium carbonate (0.311 g, 2.25 mmol) and ethyl bromoacetate (0.319 g, 1.91 mmol) was added to the solution of 3,5-dimethylmorpholine (0.2 g, 1.73 mmol) in acetonitrile (4 mL) at room temperature. The reaction mixture was stirred at 60° C. for 12 h. The reaction mixture was transferred into iced-water and extracted with ethyl acetate (20 mL×3). The combined organic layers was washed with brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to give the crude product, which was used in the next step without further purification (Crude Yield: 54%).

Workup

  1. extractionextracted with ethyl acetate (20 mL×3)
  2. washThe combined organic layers was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0f522cc89ba145daaebf66d13a53f795
Source dataset
uspto-grants-2015_08
Patent number
US09096543B2

Reaction notes

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