Sodium Hydroxide → 4-[(2-pyrrolidinyl-1H-benzimidazol-1yl)methyl]benzoic acid
Reaction equation
[N:1]1([C:6]2[N:10]([CH2:11][C:12]3[CH:21]=[CH:20][C:15]([C:16]([O:18]C)=[O:17])=[CH:14][CH:13]=3)[C:9]3[CH:22]=[CH:23][CH:24]=[CH:25][C:8]=3[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>O.CO.Cl>[N:1]1([C:6]2[N:10]([CH2:11][C:12]3[CH:13]=[CH:14][C:15]([C:16]([OH:18])=[O:17])=[CH:20][CH:21]=3)[C:9]3[CH:22]=[CH:23][CH:24]=[CH:25][C:8]=3[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1Participants
Procedure
Methyl 4-[(2-pyrrolidinyl-1H-benzimidazol-1yl)methyl]benzoate (2.5 g, 7.5 mmol) was added to a solution of sodium hydroxide (1.8 g, 45 mmol) in water (30 mL) and methanol (10 mL). The mixture was heated on a steam bath until all of the ester dissolved. Heating was continued for an additional 15 minutes and then the solution was diluted with an equal volume of water and neutralized with hydrochloric acid. The resulting precipitate was isolated by filtration, washed with water and dried to provide 1.9 g of crude product. This material was recrystallized from N,N-dimethylformamide to provide 4-[(2-pyrrolidinyl-1H-benzimidazol-1yl)methyl]benzoic acid. Analysis: Calculated for C19H19N3O2: % C, 71.01; % H, 5.96; % N, 13.07. Found: % C, 70.01; % H, 6.14; % N, 13.32.
Workup
- dissolutiondissolved
- temperatureHeating
- customThe resulting precipitate was isolated by filtration
- washwashed with water
- customdried
- customto provide 1.9 g of crude product
- customThis material was recrystallized from N,N-dimethylformamide
Sources & evidence
- ORD record
- ord-b47a2447d89d4ee6ac101de7d69275e5
- Source dataset
- uspto-grants-2004_06
- Patent number
- US06756382B2
Reaction notes
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