Methanol → HCID 131725197, compound

HRID 1061585Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[NH:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[N:15]=2)[CH2:9][CH2:8]1.[C:23]([OH:30])(=[O:29])/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27].CO>>[C:23]([OH:30])(=[O:29])/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27].[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:8][CH2:9][N:10]([CH2:13][C:14]2[NH:15][C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[N:18]=2)[CH2:11][CH2:12]1.[C:23]([OH:30])(=[O:29])/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27].[C:23]([OH:30])(=[O:29])/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27].[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:8][CH2:9][N:10]([CH2:13][C:14]2[NH:15][C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[N:18]=2)[CH2:11][CH2:12]1

Participants

Reactant 3

HCID 887Methanol

HCID 444972Fumaric Acid

HCID 50257392-((4-(2-Pyridinyl)-1-piperazinyl)methyl)-1H-benzimidazole

Product 1

HCID 131725197HCID 131725197, compound

Procedure

2-[(4-Pyridin-2-ylpiperazin-1-yl)methyl]-1H-benzimidazole (10 g, 33.7 mmol) and fumaric acid (7.8 g, 67.4 mmol) were combined in methanol (100 mL) and stirred at room temperature for 4 hours. The suspension was filtered, washed with isopropanol (60 mL), and dried under reduced pressure to provide the title compound as a solid. Elemental analysis calc'd: C, 59.09; H, 5.39; N, 14.98. Found: C, 58.97; H, 5.22; N, 14.85. DSC: sharp endotherm at 177.26° C., followed by a smaller endotherm at 237.95° C.

Workup

filtrationThe suspension was filtered
washwashed with isopropanol (60 mL)
customdried under reduced pressure

Sources & evidence

ORD record: ord-eb3a5d23ba3946e8a029b883677ca7c3
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06960589B2

Reaction notes

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