Fumaric Acid → N-(1-Phenyl-3-piperidinopropyl)quinaldinamide fumarate

HRID 34999Notes

Reaction equation

HRID 34999 reaction equation
[C:1]1([CH:7]([NH:16][C:17]([CH2:19][C:20]2[CH:29]=[CH:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=2)=[O:18])[CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]/[C:33]([OH:35])=[O:34]>C(O)C.CC(C)=O>[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]/[C:33]([OH:35])=[O:34].[C:1]1([CH:7]([NH:16][C:17]([CH2:19][C:20]2[CH:29]=[CH:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=2)=[O:18])[CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 444972Fumaric AcidHCID 67930081N-(1-phenyl-3-piperidinopropyl)quinaldinamide

Product 1

HCID 86742335N-(1-Phenyl-3-piperidinopropyl)quinaldinamide fumarateYield 78%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 702EthanolSolvent2×

Procedure

To a solution of 3.02 g (8.1 mmol.) of N-(1-phenyl-3-piperidinopropyl)quinaldinamide in a mixture of 18 ml of ethanol and 8 ml of acetone was added a solution of 0.939 g (8.1 mmol.) of fumaric acid in 20 ml of hot ethanol. The resulting mixture was stirred at room temperature and subsequently under chilling with ice. Precipitated crystals were collected by filtration and washed with acetone. The washed crystals were suspended in 60 ml of n-hexane and the suspension was refluxed for 1.5 hours. The crystals were collected by filtration, washed with n-hexane and dried. Thus, 3.10 g (yield: 78%) of the subject compound was obtained as a white crystalline product.

Workup

  1. temperaturesubsequently under chilling with ice
  2. customPrecipitated crystals
  3. filtrationwere collected by filtration
  4. washwashed with acetone
  5. temperaturethe suspension was refluxed for 1.5 hours
  6. filtrationThe crystals were collected by filtration
  7. washwashed with n-hexane
  8. customdried

Sources & evidence

ORD record
ord-c363dc78aa294123a31bd51bae97f9b1
Source dataset
uspto-grants-1988_08
Patent number
US04764617

Reaction notes

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