1-[(3-Chlorophenyl)phenylmethyl]piperazine → N-cyclopropyl-6-[4-[(3-chlorophenyl)phenylmethyl]-1-piperazinyl]hexanesulfonamide

HRID 565747Notes

Reaction equation

HRID 565747 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][CH:7]=1.[CH:21]1([NH:24][S:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]Br)(=[O:27])=[O:26])[CH2:23][CH2:22]1>C(N(CC)CC)C>[CH:21]1([NH:24][S:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][N:12]2[CH2:11][CH2:10][N:9]([CH:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:14][CH2:13]2)(=[O:27])=[O:26])[CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 45645251-[(3-Chlorophenyl)phenylmethyl]piperazineHCID 22111560N-cyclopropyl-6-bromohexanesulfonamide

Product 1

HCID 15895709N-cyclopropyl-6-[4-[(3-chlorophenyl)phenylmethyl]-1-piperazinyl]hexanesulfonamideYield 94.1%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

1-[(3-Chlorophenyl)phenylmethyl]piperazine (458.6 mg, 1.60 mmol) and N-cyclopropyl-6-bromohexanesulfonamide (500 mg, 1.76 mmol) were refluxed in triethylamine (2 ml) for 4 hours. The reaction mixture was concentrated in vacuo, and water was added thereto. The mixture was extracted with chloroform. The chloroform layer was washed with water, and dried over anhydrous magnesium sulfate. Subsequently, the solvent was removed by evaporation in vacuo. The resulting crude product was purified by column chromatography on silica gel chloroform-methanol (20:1), to give N-cyclopropyl-6-[4-[(3-chlorophenyl)phenylmethyl]-1-piperazinyl]hexanesulfonamide (737.8 mg) as an oil (yield based on 1-[(3-chlorophenyl)phenylmethyl]piperazine: 94.1%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo, and water
  2. additionwas added
  3. extractionThe mixture was extracted with chloroform
  4. washThe chloroform layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customSubsequently, the solvent was removed by evaporation in vacuo
  7. customThe resulting crude product was purified by column chromatography on silica gel chloroform-methanol (20:1)
  8. customto give

Sources & evidence

ORD record
ord-a5450ecd720a4f54a46c9bf842b1e96b
Source dataset
uspto-grants-2001_01
Patent number
US06172228B2

Reaction notes

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