Norchlorcyclizine → N-(2-hydroxyethyl)-5-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]pentanesulfonamide

HRID 565764Notes

Reaction equation

HRID 565764 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.[OH:21][CH2:22][CH2:23][NH:24][S:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]Cl)(=[O:27])=[O:26]>C(N(C(C)C)C(C)C)C>[OH:21][CH2:22][CH2:23][NH:24][S:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][N:12]1[CH2:11][CH2:10][N:9]([CH:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:14][CH2:13]1)(=[O:27])=[O:26]

Participants

4

Reactant 2

HCID 9340NorchlorcyclizineHCID 22111547N-(2-hydroxyethyl)-5-chloropentanesulfonamide

Product 1

HCID 69988227N-(2-hydroxyethyl)-5-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]pentanesulfonamideYield 91.4%

Reagents, catalysts & solvents 1

HCID 81531DiisopropylethylamineSolvent

Procedure

1-[(4-Chlorophenyl)phenylmethyl]piperazine (573.6 mg, 2.00 mmol) and N-(2-hydroxyethyl)-5-chloropentanesulfonamide (459.5 mg, 2.00 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-methanol (20:1), to give N-(2-hydroxyethyl)-5-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]pentanesulfonamide (877.0 mg) as a pale yellow oil (yield: 91.4%).

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 (20:1)

Sources & evidence

ORD record
ord-fcf8fd4d669e4a38b8c4e2ed41530e17
Source dataset
uspto-grants-2001_01
Patent number
US06172228B2

Reaction notes

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