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

HRID 565756Notes

Reaction equation

HRID 565756 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:39])(=[O:38])[C:35]([OH:37])=[O:36]>CO>[C:34]([OH:39])(=[O:38])[C:35]([OH:37])=[O:36].[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 971Oxalic AcidHCID 15895709N-cyclopropyl-6-[4-[(3-chlorophenyl)phenylmethyl]-1-piperazinyl]hexanesulfonamide

Product 1

HCID 22111595N-cyclopropyl-6-[4-[(3-chlorophenyl)phenylmethyl]-1-piperazinyl]hexanesulfonamide oxalateYield 71.8%

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 (50 ml). Oxalic acid dehydrate (0.32 g, 2.55 mmol) was added thereto. After dissolving the mixture with heating, the solvent was removed by evaporation in vacuo. Acetone was added to the residue, and the precipitated crystals were collected by filtration. The crystals were recrystallized from acetone, to give N-cyclopropyl-6-[4-[(3-chlorophenyl)phenylmethyl]-1-piperazinyl]hexanesulfonamide oxalate (0.85 g) as colorless crystals (yield based on N-cyclopropyl-6-[4-[(3-chlorophenyl)phenylmethyl]-1-piperazinyl]hexanesulfonamide: 71.8%).

Workup

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

Sources & evidence

ORD record
ord-31250b2ecc12462fab57b5aea4c1ed62
Source dataset
uspto-grants-2001_01
Patent number
US06172228B2

Reaction notes

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