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

HRID 565787Notes

Reaction equation

HRID 565787 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]Cl)(=[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 11010063N-cyclopropyl-6-chlorohexanesulfonamide

Product 1

HCID 15895709N-cyclopropyl-6-[4-[(3-chlorophenyl)phenylmethyl]-1-piperazinyl]hexanesulfonamideYield 51.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-[(3-Chlorophenyl)phenylmethyl]piperazine (543.7 mg, 1.90 mmol) and N-cyclopropyl-6-chlorohexanesulfonamide (500 mg, 2.09 mmol) were refluxed in toluene (15 ml) in the presence of triethylamine (211 mg, 2.09 mmol) for 48 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 (482.7 mg) as an oil (yield based on 1-[(3-chlorophenyl)phenylmethyl]piperazine: 52.0%).

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-14110c8072074ccda7f89bcaddc1e73c
Source dataset
uspto-grants-2001_01
Patent number
US06172228B2

Reaction notes

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