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

HRID 565753Notes

Reaction equation

HRID 565753 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.Cl[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][S:28]([NH2:31])(=[O:30])=[O:29]>C(N(C(C)C)C(C)C)C>[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[CH2:10][CH2:11][N:12]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][S:28]([NH2:31])(=[O:30])=[O:29])[CH2:13][CH2:14]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 45645251-[(3-Chlorophenyl)phenylmethyl]piperazineHCID 221115356-Chlorohexanesulfonamide

Product 1

HCID 158957156-[4-[(3-Chlorophenyl)phenylmethyl]1-piperazinyl]hexanesulfonamideYield 95.6%

Reagents, catalysts & solvents 1

HCID 81531DiisopropylethylamineSolvent

Procedure

1-[(3-Chlorophenyl)phenylmethyl]piperazine (500 mg, 1.74 mmol) and 6-chlorohexanesulfonamide (383 mg, 1.92 mmol) synthesized referring to a process described in J. Org. Chem. 52, 2162 (1987) were refluxed in N-ethyldiisopropylamine (5 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 (100:3), to give 6-[4-[(3-chlorophenyl)phenylmethyl]1-piperazinyl]hexanesulfonamide (749 mg) as a colorless oil (yield based on 1-[(3-chlorophenyl)phenylmethyl]piperazine: 95.4%).

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 (100:3)
  8. customto give

Sources & evidence

ORD record
ord-9c7a861338be4affafa73ac4182f3416
Source dataset
uspto-grants-2001_01
Patent number
US06172228B2

Reaction notes

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