4-[2-(4-Chlorophenyl)ethoxy]benzaldehyde → 1-Butyl-2-{4-[2-(4-chlorophenyl)ethoxy]-phenyl}-6-(2-pyrrolidin-1-yl-ethoxy)-1h-benzimidazole

HRID 2236967Notes

Reaction equation

HRID 2236967 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][C:11]2[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.[CH2:19]([NH:23][C:24]1[C:25]([NH2:38])=[CH:26][CH:27]=[C:28]([O:30][CH2:31][CH2:32][N:33]2[CH2:37][CH2:36][CH2:35][CH2:34]2)[CH:29]=1)[CH2:20][CH2:21][CH3:22]>C(O)C>[CH2:19]([N:23]1[C:24]2[CH:29]=[C:28]([O:30][CH2:31][CH2:32][N:33]3[CH2:37][CH2:36][CH2:35][CH2:34]3)[CH:27]=[CH:26][C:25]=2[N:38]=[C:15]1[C:14]1[CH:17]=[CH:18][C:11]([O:10][CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:12][CH:13]=1)[CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 713506694-[2-(4-Chlorophenyl)ethoxy]benzaldehydeHCID 91069588n2-Butyl-4-(2-pyrrolidin-1-ylethoxy)-benzene-1,2-diamine

Product 1

HCID 596991341-Butyl-2-{4-[2-(4-chlorophenyl)ethoxy]-phenyl}-6-(2-pyrrolidin-1-yl-ethoxy)-1h-benzimidazoleYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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%).

Workup

  1. customThis compound was prepared
  2. temperatureby refluxing
  3. customEthanol was removed in vacuo
  4. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-0ca12cb655a04d7286fac8f73fc4cb9e
Source dataset
uspto-grants-2010_05
Patent number
US07714013B2

Reaction notes

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