Water → methyl 4-[(2-pyrrolidinyl-1H-benzimidazol-1yl)methyl]benzoate

HRID 1280477

Reaction equation

HRID 1280477 reaction equation
[H-].[Na+].[N:3]1([C:8]2[NH:12][C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[N:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4]1.Br[CH2:18][C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=1.O>CN(C)C=O>[N:3]1([C:8]2[N:9]([CH2:18][C:19]3[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=3)[C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 256687Methyl 4-(bromomethyl)benzoateHCID 69918962-(Pyrrolidin-1-yl)-1H-benzo[d]imidazole

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (402 mg, 11 mmol) was added to a suspension of 2-pyrrolidino-1H-benzimidazole (1.9 g, 10.1 mmol) in dry N,N-dimethylformamide (30 mL). All solids dissolved. The solution was allowed to stir at ambient temperature for 15 minutes following the cessation of foaming. The solution was cooled to 5° C. and a solid formed. Methyl 4-(bromomethyl)benzoate (2.1 g, 01 mol) was added to the suspension and all the solids dissolved. The solution was allowed to stir at ambient temperature and a solid formed. The mixture was stirred at ambient temperature overnight and then it was poured into cold water. A solid was isolated by filtration, washed with water and dried to provide 3.0 g of crude product as an off-white solid. This material was recrystallized from methanol to provide methyl 4-[(2-pyrrolidinyl-1H-benzimidazol-1yl)methyl]benzoate. Analysis: Calculated for C20H21N3O2: %C, 71.62; %H, 6.31; %N, 12.53; Found: %C, 71.44; %H, 6.41; %N, 12.50.

Workup

  1. dissolutionAll solids dissolved
  2. temperatureThe solution was cooled to 5° C.
  3. customa solid formed
  4. dissolutiondissolved
  5. stirringto stir at ambient temperature
  6. customa solid formed
  7. stirringThe mixture was stirred at ambient temperature overnight
  8. customA solid was isolated by filtration
  9. washwashed with water
  10. customdried
  11. customto provide 3.0 g of crude product as an off-white solid
  12. customThis material was recrystallized from methanol

Sources & evidence

ORD record
ord-b22b45f049244b709cfcdbd900967b03
Source dataset
uspto-grants-2002_09
Patent number
US06451810B1

Linked notes

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