Potassium Carbonate → 3-Phenyl-4-(4-chlorophenacyl)-2-piperazinone

HRID 622776Notes

Reaction equation

HRID 622776 reaction equation
[C:1]1([CH:7]2[NH:12][CH2:11][CH2:10][NH:9][C:8]2=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:20][C:21]1[CH:30]=[CH:29][C:24]([C:25](=[O:28])[CH2:26]Br)=[CH:23][CH:22]=1>ClCCl>[C:1]1([CH:7]2[N:12]([CH2:26][C:25]([C:24]3[CH:29]=[CH:30][C:21]([Cl:20])=[CH:22][CH:23]=3)=[O:28])[CH2:11][CH2:10][NH:9][C:8]2=[O:13])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 68303p-Chlorophenacyl bromideHCID 2506813-Phenylpiperazin-2-one

Product 1

HCID 143023373-Phenyl-4-(4-chlorophenacyl)-2-piperazinoneYield 85.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred mixture of 58.0 g (0.33 mol) of 3-phenyl-2-piperazinone, 85 g (0.62 mol) of blended potassium carbonate, and 76.9 g (0.33 mol) of 4-chlorophenacyl bromide in 400 ml of dichloromethane was heated at reflux for 12 hours. The mixture was cooled to ambient temperature, filtered, and the solid washed thoroughly with dichloromethane. The filtrate was concentrated to dryness, isopropanol added and stirred, the solid collected by filtration, washed thoroughly with isopropanol and dried in a vacuum oven at 50° C. to give 92.5 g (85 %) of 3-phenyl-4-(4-chlorophenacyl)-2-piperazinone. This material was used in Example 2 of the process. Pure material could be obtained by recrystallization from methanol to give a white solid (mp. 157°-158° C. dec.).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 12 hours
  3. filtrationfiltered
  4. washthe solid washed thoroughly with dichloromethane
  5. concentrationThe filtrate was concentrated to dryness, isopropanol
  6. additionadded
  7. filtrationthe solid collected by filtration
  8. washwashed thoroughly with isopropanol
  9. customdried in a vacuum oven at 50° C.

Sources & evidence

ORD record
ord-6a1993b05f734e0aa7f7a6bf36cbafa5
Source dataset
uspto-grants-1988_09
Patent number
US04772705

Reaction notes

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