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

HRID 565754Notes

Reaction equation

HRID 565754 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]>C(O)C>[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 444972Fumaric AcidHCID 15895709N-cyclopropyl-6-[4-[(3-chlorophenyl)phenylmethyl]-1-piperazinyl]hexanesulfonamide

Product 1

HCID 22111604N-cyclopropyl-6-[4-[(3-chlorophenyl)phenylmethyl]-1-piperazinyl]hexanesulfonamide fumarateYield 93.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-Cyclopropyl-6-[4-[(3-chlorophenyl)phenylmethyl]-1-piperazinyl]hexanesulfonamide (13.03 g, 26.59 mmol) prepared in the same manner as in Example 1 was dissolved in ethanol (100 ml). Fumaric acid (4.01 g, 34.55 mmol) was added thereto. After dissolving the mixture with heating, the mixture was cooled in an ice bath to allow the mixture to crystallize. The crystals were filtered, washed with a small amount of ethanol, and dried at 80° C. in vacuo, to give N-cyclopropyl-6-[4-[(3-chlorophenyl)phenylmethyl]-1-piperazinyl]hexanesulfonamide fumarate (15.11 g) as colorless prisms (yield based on N-cyclopropyl-6-[4-[(3-chlorophenyl)phenylmethyl]-1-piperazinyl]hexanesulfonamide: 93.7%).

Workup

  1. dissolutionAfter dissolving the mixture
  2. temperaturewith heating
  3. temperaturethe mixture was cooled in an ice bath
  4. customto crystallize
  5. filtrationThe crystals were filtered
  6. washwashed with a small amount of ethanol
  7. customdried at 80° C. in vacuo
  8. customto give

Sources & evidence

ORD record
ord-81a4245d6a364764a3d2449a5162e2e5
Source dataset
uspto-grants-2001_01
Patent number
US06172228B2

Reaction notes

Loading…