Triethylamine → 4-(2,3-Dichlorobenzoyl)piperazin-2-one

HRID 1888979Notes

Reaction equation

HRID 1888979 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][C:2]1=[O:7].C(N(CC)CC)C.[Cl:15][C:16]1[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:17]=1[C:18](Cl)=[O:19]>ClCCl.C([O-])(O)=O.[Na+]>[Cl:15][C:16]1[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:17]=1[C:18]([N:4]1[CH2:5][CH2:6][NH:1][C:2](=[O:7])[CH2:3]1)=[O:19]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 179442,3-Dichlorobenzoyl chlorideHCID 231360Piperazin-2-one

Product 1

HCID 310960434-(2,3-Dichlorobenzoyl)piperazin-2-one

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a suspension of 2-piperazinone (5.3 g, 52.9 mmol, commercially available e.g. from Sigma-Aldrich) in dry Dichloromethane (DCM) (76 ml) was added triethylamine (16.23 ml, 116 mmol) and finally 2,3-dichlorobenzoyl chloride (12.20 g, 58.2 mmol, commercially available e.g. from ABCR, ChemPacific or UkrOrgSynthesis) dropwise (exothermic). The mixture was stirred at room temperature. After 1 hour the mixture was diluted with Dichloromethane (DCM) (150 mL) and saturated NaHCO3 solution (150 ml), the phases were separated and the aqueous layer was extracted with DCM (2×100 ml). The combined organic fractions were washed with brine and dried over MgSO4. Evaporation gave 4-[(2,3-dichlorophenyl)carbonyl]-2-piperazinone (12 g).

Workup

  1. customthe phases were separated
  2. extractionthe aqueous layer was extracted with DCM (2×100 ml)
  3. washThe combined organic fractions were washed with brine
  4. dry with materialdried over MgSO4
  5. customEvaporation

Sources & evidence

ORD record
ord-146fdf2700e149978f369c205f940190
Source dataset
uspto-grants-2013_08
Patent number
US08501946B2

Reaction notes

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