N,N'-Dimethylethylenediamine → 4-(4-Bromophenyl)morpholin-3-one

HRID 2206236Notes

Reaction equation

HRID 2206236 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][C:2]1=[O:7].[Br:8][C:9]1[CH:14]=[CH:13][C:12](I)=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CNCCNC>CN(C=O)C.[Cu]I.O>[Br:8][C:9]1[CH:14]=[CH:13][C:12]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][C:2]2=[O:7])=[CH:11][CH:10]=1

Participants

8

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 10796Cesium carbonateHCID 115221-Bromo-4-iodobenzeneHCID 669533-Morpholinone

Product 1

HCID 179827074-(4-Bromophenyl)morpholin-3-oneYield 82.9%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of morpholin-3-one (100 mg), 1-bromo-4-iodobenzene (282 mg), cesium carbonate (326 mg) and N1,N2-dimethylethane-1,2-diamine (9 mg) in DMF (2 mL) was added copper(I) iodide (10 mg) at room temperature under nitrogen atmosphere. The reaction mixture was stirred under microwave irradiation at 100° C. for 30 min. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (210 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-288a746c692345e08e7deb0de5d70455
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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