1-[4-Chlorophenyl-(2-pyridyl)methyl]piperazine → N-cyclopropyl-6-[4-[4-chlorophenyl-(2-pyridyl)methyl]-1-piperazinyl]hexanesulfonamide

HRID 565752Notes

Reaction equation

HRID 565752 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[CH:21]1([NH:24][S:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]Cl)(=[O:27])=[O:26])[CH2:23][CH2:22]1>C(N(C(C)C)C(C)C)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:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[CH2:14][CH2:13]2)(=[O:27])=[O:26])[CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 33976181-[4-Chlorophenyl-(2-pyridyl)methyl]piperazineHCID 11010063N-cyclopropyl-6-chlorohexanesulfonamide

Product 1

HCID 15895713N-cyclopropyl-6-[4-[4-chlorophenyl-(2-pyridyl)methyl]-1-piperazinyl]hexanesulfonamideYield 46.6%

Reagents, catalysts & solvents 1

HCID 81531DiisopropylethylamineSolvent

Procedure

1-[4-Chlorophenyl-(2-pyridyl)methyl]piperazine (7.90 g, 27.5 mmol) and N-cyclopropyl-6-chlorohexanesulfonamide (7.24 g, 30.2 mmol) were refluxed in N-ethyldiisopropylamine (20 ml) for 6 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 with chloroform-methanol (20:1), to give N-cyclopropyl-6-[4-[4-chlorophenyl-(2-pyridyl)methyl]-1-piperazinyl]hexanesulfonamide (6.29 g) as an oil (yield based on 1-[4-chlorophenyl-(2-pyridyl)methyl]piperazine: 92.7%).

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 with chloroform-methanol (20:1)
  8. customto give

Sources & evidence

ORD record
ord-14d07d286b834c91b7739b163ce4d590
Source dataset
uspto-grants-2001_01
Patent number
US06172228B2

Reaction notes

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