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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2206236Generated: November 1, 2026

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

https://huagongshe.com/reaction/2206236

Reaction equation

Participants

RoleNameHCIDCharge
ReactantN,N'-DimethylethylenediamineHCID 8070—
ReactantCesium carbonateHCID 10796—
Reactant1-Bromo-4-iodobenzeneHCID 11522—
Reactant3-MorpholinoneHCID 66953—
CatalystCopper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 24350—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
Product4-(4-Bromophenyl)morpholin-3-oneHCID 1798270782.9%

Reaction Conditions

Temperature100 °C

Reaction Steps

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).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09371320B2
Source datasetuspto-grants-2016_06
ORD IDord-288a746c692345e08e7deb0de5d70455
Source noteuspto-grants-2016_06