Norchlorcyclizine → N-cyclopropyl-10-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]decanesulfonamide

HRID 565776Notes

Reaction equation

HRID 565776 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][CH: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][CH2:34][CH2:35][CH2:36][CH2:37]Br)(=[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][CH2:34][CH2:35][CH2:36][CH2:37][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:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:14][CH2:13]2)(=[O:27])=[O:26])[CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 9340NorchlorcyclizineHCID 22111539N-cyclopropyl-10-bromodecanesulfonamide

Product 1

HCID 69988589N-cyclopropyl-10-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]decanesulfonamideYield 96.4%

Reagents, catalysts & solvents 1

HCID 81531DiisopropylethylamineSolvent

Procedure

1-[(4-Chlorophenyl)phenylmethyl]piperazine (525.0 mg, 1.83 mmol) and N-cyclopropyl-10-bromodecanesulfonamide (685.0 mg, 2.01 mmol) were refluxed in N-ethyldiisopropylamine (2 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, to give N-cyclopropyl-10-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]decanesulfonamide (964.0 mg) as a pale brown oil (yield based on 1-[(4-chlorophenyl)phenylmethyl]piperazine: 96.5%).

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
  8. customto give

Sources & evidence

ORD record
ord-6a304dd0462648c0b8b6c7e541742f76
Source dataset
uspto-grants-2001_01
Patent number
US06172228B2

Reaction notes

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