Piperazin-2-one → HCID 51034692, compound

HRID 469265Notes

Reaction equation

HRID 469265 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][C:2]1=[O:7].[N:8]([CH:11]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[C:9]=[O:10]>ClCCl>[CH:11]([NH:8][C:9]([N:4]1[CH2:5][CH2:6][NH:1][C:2](=[O:7])[CH2:3]1)=[O:10])([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 231360Piperazin-2-oneHCID 4250935(Isocyanatomethylene)dibenzene

Product 1

HCID 51034692HCID 51034692, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of piperazin-2-one (100 mg, 1 mmol) was added (isocyanatomethylene)dibenzene (209 mg, 1 mmol) in dichloromethane (5 mL). The solution was stirred for 2 hours at room temperature and concentrated in vacuo. The residue was diluted with EtOAc and then 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 desired compound N-benzhydryl-3-oxopiperazine-1-carboxamide (Compound 1) (232 mg, 75%) as a white powder.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with EtOAc
  3. washwashed 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-60572406aa7d41e09af1ff9530a6974e
Source dataset
uspto-grants-2014_01
Patent number
US08629149B2

Reaction notes

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