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

HRID 565755Notes

Reaction equation

HRID 565755 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.[C:34]([OH:41])(=[O:40])/[CH:35]=[CH:36]\[C:37]([OH:39])=[O:38]>CO>[C:34]([OH:41])(=[O:40])/[CH:35]=[CH:36]\[C:37]([OH:39])=[O:38].[C:34]([OH:41])(=[O:40])/[CH:35]=[CH:36]\[C:37]([OH:39])=[O:38].[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

Participants

4

Reactant 2

HCID 444266Maleic AcidHCID 15895709N-cyclopropyl-6-[4-[(3-chlorophenyl)phenylmethyl]-1-piperazinyl]hexanesulfonamide

Product 1

HCID 86756218N-cyclopropyl-6-[4-[(3-chlorophenyl)phenylmethyl]-1-piperazinyl]hexanesulfonamide dimaleateYield 50.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-Cyclopropyl-6-[4-[(3-chlorophenyl)phenylmethyl]-1-piperazinyl]hexanesulfonamide (253 mg, 0.52 mmol) prepared in the same manner as in Example 1 was dissolved in methanol (15 ml). Maleic acid (138 mg, 1.19 mmol) was added thereto. After dissolving the mixture with heating, the solvent was removed by evaporation in vacuo. Acetone-diethyl ether was added to the residue, and the precipitated crystals were collected by filtration. The crystals were recrystallized from ethyl acetate, to give N-cyclopropyl-6-[4-[(3-chlorophenyl)phenylmethyl]-1-piperazinyl]hexanesulfonamide dimaleate (189 mg) as colorless prisms (yield based on N-cyclopropyl-6-[4-[(3-chlorophenyl)phenylmethyl]-1-piperazinyl)hexanesulfonamide: 50.3%).

Workup

  1. dissolutionAfter dissolving the mixture
  2. temperaturewith heating
  3. customthe solvent was removed by evaporation in vacuo
  4. additionAcetone-diethyl ether was added to the residue
  5. filtrationthe precipitated crystals were collected by filtration
  6. customThe crystals were recrystallized from ethyl acetate
  7. customto give

Sources & evidence

ORD record
ord-131df067850048a6ac5e768697bd022f
Source dataset
uspto-grants-2001_01
Patent number
US06172228B2

Reaction notes

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