4-Bromobenzoyl chloride → HCID 57849479, compound

HRID 737125Notes

Reaction equation

HRID 737125 reaction equation
[C:1]1([CH:7]2[CH2:12][NH:11][CH2:10][CH2:9][NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1>ClCCl>[Br:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([N:11]2[CH2:10][CH2:9][NH:8][CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:12]2)=[O:19])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 685154-Bromobenzoyl chlorideHCID 2506732-Phenylpiperazine

Product 1

HCID 57849479HCID 57849479, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

This compound could be made in the following manner: 500 mg of 2-phenylpiperazine would be dissolved in dichloromethane and cooled to 0° C. A solution of 0.5 equiv. of 4-bromobenzoyl chloride in dichloromethane would be added dropwise over 1 h at 0° C. The reaction would be stirred at 0° C. for 0.5 h, then allowed to warm to room temperature and stirred for a further 3 h until complete conversion. The reaction mixture would be diluted with dichloromethane, washed with 1M aqueous sodium hydroxide solution and brine, then dried over sodium sulfate, filtered and concentrated in vacuo. The crude residue would be purified by column chromatography to afford (4-bromo-phenyl)-(3-phenyl-piperazin-1-yl)-methanone.

Workup

  1. customThe reaction
  2. temperatureto warm to room temperature
  3. stirringstirred for a further 3 h until complete conversion
  4. washwashed with 1M aqueous sodium hydroxide solution and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue would be purified by column chromatography

Sources & evidence

ORD record
ord-9d7d4413c726459ea41f9b8dcbe5882c
Source dataset
uspto-grants-2009_09
Patent number
US07595397B2

Reaction notes

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