N,N'-Dimethylethylenediamine → HCID 58484832, compound

HRID 1804411Notes

Reaction equation

HRID 1804411 reaction equation
Br[C:2]1[CH:24]=[CH:23][C:5]([C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=3[CH3:21])[C:10](=[O:22])[CH2:9]2)=[O:7])=[C:4]([S:25]([CH3:28])(=[O:27])=[O:26])[CH:3]=1.[O:29]1[CH2:33][CH2:32][NH:31][C:30]1=[O:34].C(=O)([O-])[O-].[K+].[K+].CNCCNC>[Cu]I.O.C1(C)C=CC=CC=1>[CH3:21][C:15]1[CH:16]=[C:17]([CH3:20])[CH:18]=[CH:19][C:14]=1[N:11]1[CH2:12][CH2:13][N:8]([C:6]([C:5]2[CH:23]=[CH:24][C:2]([N:31]3[CH2:32][CH2:33][O:29][C:30]3=[O:34])=[CH:3][C:4]=2[S:25]([CH3:28])(=[O:27])=[O:26])=[O:7])[CH2:9][C:10]1=[O:22]

Participants

8

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 739492-OxazolidinoneHCID 67381202HCID 67381202, compound

Product 1

HCID 58484832HCID 58484832, compoundYield 63.9%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a mixture of 4-(4-bromo-2-methanesulfonylbenzoyl)-1-(2,4-dimethylphenyl)piperazin-2-one (931 mg), oxazolidin-2-one (209 mg), potassium carbonate (849 mg) and copper (I) iodide (76 mg) were added toluene (2 mL) and N,N′-dimethylethylenediamine (90 μL), and the mixture was refluxed for 8 hr. After cooling, water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and the solvent was evaporated. The residue was purified by column chromatography (chloroform:methanol) and recrystallized from a mixed solution of hexane and ethyl acetate to give the title compound (603 mg).

Workup

  1. temperaturethe mixture was refluxed for 8 hr
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with chloroform
  4. washThe organic layer was washed with saturated brine
  5. customthe solvent was evaporated
  6. customThe residue was purified by column chromatography (chloroform:methanol)
  7. customrecrystallized from a mixed solution of hexane and ethyl acetate

Sources & evidence

ORD record
ord-106dcf89bc8f4c8b9084aae57f843d46
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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