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

HRID 565788Notes

Reaction equation

HRID 565788 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>C1(C)C=CC=CC=1>[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

5

Reactant 3

HCID 8471TriethylamineHCID 45645251-[(3-Chlorophenyl)phenylmethyl]piperazineHCID 22111560N-cyclopropyl-6-bromohexanesulfonamide

Product 1

HCID 15895709N-cyclopropyl-6-[4-[(3-chlorophenyl)phenylmethyl]-1-piperazinyl]hexanesulfonamideYield 67%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-[(3-Chlorophenyl)phenylmethyl]piperazine (435.2 mg, 1.52 mmol) and N-cyclopropyl-6-bromohexanesulfonamide (474.5 mg, 1.67 mmol) were refluxed in toluene (15 ml) in the presence of triethylamine (169 mg, 1.67 mmol) for 42 hours. The reaction mixture was washed with water, and the organic layer was 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-[(3-chlorophenyl)phenylmethyl]-1-piperazinyl]hexanesulfonamide (499.0 mg) as an oil (yield based on 1-[(3-chlorophenyl)phenylmethyl]piperazine: 67.1%).

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. customSubsequently, the solvent was removed by evaporation in vacuo
  4. customThe resulting crude product was purified by column chromatography on silica gel with chloroform-methanol (20:1)
  5. customto give

Sources & evidence

ORD record
ord-b74b788f9326498396d2f2a0e1d5cc85
Source dataset
uspto-grants-2001_01
Patent number
US06172228B2

Reaction notes

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