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

HRID 565758
Notes
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Reaction equation

HRID 565758 reaction equation
[CH:1]1([NH:4][S:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][N:17]([CH:20]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:16][CH2:15]2)(=[O:7])=[O:6])[CH2:3][CH2:2]1.[ClH:34].CO>CO>[ClH:33].[ClH:34].[CH:1]1([NH:4][S:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][N:17]([CH:20]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:16][CH2:15]2)(=[O:7])=[O:6])[CH2:3][CH2:2]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 15895709N-cyclopropyl-6-[4-[(3-chlorophenyl)phenylmethyl]-1-piperazinyl]hexanesulfonamideHCID 21893726Hydrochloride methanol

Product 1

HCID 22111564N-cyclopropyl-6-[-4-[(3-chlorophenyl)phenylmethyl]-1-piperazinyl]hexanesulfonamide dihydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-Cyclopropyl-6-[4-[(3-chlorophenyl)phenylmethyl]-1-piperazinyl]hexanesulfonamide (1.00 g, 2.04 mmol) prepared in the same manner as in Example 1 was dissolved in methanol (10 ml). A 15% HCl-methanol solution was added thereto to make the solution acidic, and the solvent was then removed by evaporation in vacuo. Acetone was added to the residue, and the precipitated crystals were collected by filtration. The crystals were recrystallized from ethanol, to give N-cyclopropyl-6-[-4-[(3-chlorophenyl)phenylmethyl]-1-piperazinyl]hexanesulfonamide dihydrochloride (0.87 g) as colorless prisms (yield based on N-cyclopropyl-6-[-4-[(3-chlorophenyl)phenylmethyl]-1-piperazinyl]hexanesulfonamide: 75.7%).

Workup

  1. customthe solvent was then removed by evaporation in vacuo
  2. additionAcetone was added to the residue
  3. filtrationthe precipitated crystals were collected by filtration
  4. customThe crystals were recrystallized from ethanol
  5. customto give

Sources & evidence

ORD record
ord-32ffb4f791364a31baeee8504def890d
Source dataset
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06172228B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes