O-Phenylenediamine → 2-[4-[3-(1-pyrrolidinyl)propoxy]phenyl]-1H-benzimidazole

HRID 36343Notes

Reaction equation

HRID 36343 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH2:8].[N:9]1([CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=2)[CH2:13][CH2:12][CH2:11][CH2:10]1.S(=O)(O)[O-].[Na+]>CO>[N:9]1([CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:25]=[CH:24][C:21]([C:22]3[NH:8][C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[N:1]=3)=[CH:20][CH:19]=2)[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 7243O-PhenylenediamineHCID 116515734-(3-Pyrrolidin-1-ylpropoxy)benzaldehydeHCID 23665763Sodium Bisulfite

Product 1

HCID 152915822-[4-[3-(1-pyrrolidinyl)propoxy]phenyl]-1H-benzimidazoleYield 34%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1,2-Diaminobenzene (4.65 g), 4-[3-(1-pyrrolidinyl)propoxy]benzaldehyde (Step B) (10.0 g) and sodium bisulfite (4.60 g) are stirred at reflux in methanol (300 mL) for 14 hours. The mixture is filtered and evaporated. The residue is recrystallized from hot ethyl acetate/ethanol to give 4.68 g of the title compound as a yellow solid.

Workup

  1. filtrationThe mixture is filtered
  2. customevaporated
  3. customThe residue is recrystallized from hot ethyl acetate/ethanol

Sources & evidence

ORD record
ord-8821c957c0154351b1980809148be464
Source dataset
uspto-grants-1995_05
Patent number
US05414010

Reaction notes

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