1,2-Dichloroethane → 4-(3,3-Diphenylpropanoyl)piperazin-2-one

HRID 469261

Reaction equation

HRID 469261 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][C:2]1=[O:7].[C:8]1([CH:14]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:15][C:16](O)=[O:17])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(Cl)CCl>ClCCl>[C:19]1([CH:14]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:15][C:16]([N:4]2[CH2:5][CH2:6][NH:1][C:2](=[O:7])[CH2:3]2)=[O:17])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 64798Diphenylpropionic acidHCID 231360Piperazin-2-one

Product 1

HCID 223131444-(3,3-Diphenylpropanoyl)piperazin-2-oneYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of piperazin-2-one (100 m g, 1 mmol), 3,3-diphenylpropanoic acid (226 mg, 1 mmol) was added EDC (382 mg, 2 mmol) in dichloromethane (5 mL). The solution was stirred at room temperature overnight and concentrated in vacuo. The residue was diluted with EtOAc, and the mixture was washed consecutively with saturated aqueous NaHCO3 and brine. The organic layer was dried (Na2SO4), filtered, and concentrated in vacuo. The crude material was purified by flash column chromatography (2:98 MeOH/DCM) to give the desired 4-(3,3-diphenylpropanoyl)piperazin-2-one product (compound 4) (246 mg, 80%) as a white powder.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with EtOAc
  3. washthe mixture was washed consecutively with saturated aqueous NaHCO3 and brine
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by flash column chromatography (2:98 MeOH/DCM)

Sources & evidence

ORD record
ord-d5dbfa3155804983a8a3fd52a2d9a10c
Source dataset
uspto-grants-2014_01
Patent number
US08629149B2

Linked notes

Loading…