Sodium Hydroxide → 4-[(2-pyrrolidinyl-1H-benzimidazol-1yl)methyl]benzoic acid

HRID 746500Notes

Reaction equation

HRID 746500 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]1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 12144533methyl 4-[(2-pyrrolidinyl-1H-benzimidazol-1yl)methyl]benzoate

Product 1

HCID 121445344-[(2-pyrrolidinyl-1H-benzimidazol-1yl)methyl]benzoic acid

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent2×

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

  1. dissolutiondissolved
  2. temperatureHeating
  3. customThe resulting precipitate was isolated by filtration
  4. washwashed with water
  5. customdried
  6. customto provide 1.9 g of crude product
  7. customThis material was recrystallized from N,N-dimethylformamide

Sources & evidence

ORD record
ord-cd724d5fe5f041baba1e9da0b4b8f9be
Source dataset
uspto-grants-2008_07
Patent number
US07393859B2

Reaction notes

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