N,N'-Dimethylethylenediamine → 3-{4-[4-(4-Chlorobenzoyl)piperidine-1-carbonyl]-3-methanesulfonylphenyl}oxazolidin-2-one

HRID 1803967Notes

Reaction equation

HRID 1803967 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][CH:13]([C:16](=[O:24])[C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)=[O:9])=[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>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([C:16]([CH:13]2[CH2:14][CH2:15][N:10]([C:8]([C:5]3[CH:6]=[CH:7][C:2]([N:31]4[CH2:32][CH2:33][O:29][C:30]4=[O:34])=[CH:3][C:4]=3[S:25]([CH3:28])(=[O:27])=[O:26])=[O:9])[CH2:11][CH2:12]2)=[O:24])=[CH:18][CH:19]=1

Participants

8

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 739492-OxazolidinoneHCID 67380967(4-Bromo-2-methanesulfonylphenyl)[4-(4-chlorobenzoyl)piperidin-1-yl]methanone

Product 1

HCID 547550043-{4-[4-(4-Chlorobenzoyl)piperidine-1-carbonyl]-3-methanesulfonylphenyl}oxazolidin-2-oneYield 64.6%

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-bromo-2-methanesulfonylphenyl)[4-(4-chlorobenzoyl)piperidin-1-yl]methanone (1.5 g), which is the intermediate described in Preparation Example 24, oxazolidin-2-one (313 mg), potassium carbonate (829 mg) and copper (I) iodide (114 mg) were added toluene (3 mL) and N,N′-dimethylethylenediamine (130 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) to give the title compound (982 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)

Sources & evidence

ORD record
ord-c752880e41ed4b82aea64a979143abaa
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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