Fumaric Acid → 4-Amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methoxyphenyl)benzamide hemifumarate

HRID 2528

Reaction equation

HRID 2528 reaction equation
[NH2:1][C:2]1[CH:35]=[CH:34][C:5]([C:6]([N:8]([CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][CH:22]([C:25](=[O:33])[C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[CH2:21][CH2:20]2)[C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=2)=[O:7])=[CH:4][CH:3]=1.[C:36]([OH:43])(=[O:42])/[CH:37]=[CH:38]/[C:39]([OH:41])=[O:40]>CO>[C:36]([OH:43])(=[O:42])/[CH:37]=[CH:38]/[C:39]([OH:41])=[O:40].[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:8]([CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][CH:22]([C:25](=[O:33])[C:26]3[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=3)[CH2:21][CH2:20]2)[C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=2)=[O:7])=[CH:34][CH:35]=1.[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:8]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=2)[CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][CH:22]([C:25](=[O:33])[C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[CH2:21][CH2:20]2)=[O:7])=[CH:34][CH:35]=1

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 196898814-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methoxyphenyl)benzamide

Product 1

HCID 1317205694-Amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methoxyphenyl)benzamide hemifumarateYield 90.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

4-Amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methoxyphenyl)benzamide (475.0 mg, 1.00 mmol) was dissolved in methanol (4.0 ml) and mixed with a methanol solution (3.0 ml) of fumaric acid (58.0 mg, 0.50 mmol) at 0° C. Thereafter, the thus precipitated crystals were collected by filtration and recrystallized from an ethanol-water mixture solution to obtain 481.0 mg (90.0%) of the title compound in a colorless powder form.

Workup

  1. filtrationThereafter, the thus precipitated crystals were collected by filtration
  2. customrecrystallized from an ethanol-water mixture solution

Sources & evidence

ORD record
ord-a962f676bde548c9a208b5b8ceb746c5
Source dataset
uspto-grants-1998_03
Patent number
US05728835

Linked notes

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