Reaction #45921

Reaction equation

4-[2-(4-chloro-phenyl)-ethoxy]-bezaldehyde

N2-Butyl-4-(2-pyrrolidin-1-ylethoxy)-benzene-1,2-diamine

→

1-butyl-2-{4-[2-(4-chlorophenyl)ethoxy]-phenyl}-6-(2-pyrrolidin-1-yl-ethoxy)-1H-benzimidazole

Yield 40.0%

Solvents

ethanol

Conditions

Workup

1. 1
   OtherThis compound was prepared
2. 2
   Temperatureby refluxing
3. 3
   OtherEthanol was removed in vacuo
4. 4
   Otherthe residue was purified by silica gel chromatography

Procedure

This compound was prepared according to the General Procedure K by refluxing a mixture of 4-[2-(4-chloro-phenyl)-ethoxy]-bezaldehyde (synthesized via General Procedure A) (100 mg) and N2-Butyl-4-(2-pyrrolidin-1-ylethoxy)-benzene-1,2-diamine (synthesized via General Procedures G1 and G2 and H) (50 mg) in ethanol overnight. Ethanol was removed in vacuo and the residue was purified by silica gel chromatography using 5% MeOH in DCM to give pure 1-butyl-2-{4-[2-(4-chlorophenyl)ethoxy]-phenyl}-6-(2-pyrrolidin-1-yl-ethoxy)-1H-benzimidazole (37.0 mg, 40%).

Source