2-Butylamino-4,6-di(3-diethylaminopropoxy)aniline → (3-(1-Butyl-2-{4-[2-(4-chlorophenyl)-ethoxy]-phenyl}-6-(3-diethylaminopropoxy)-1h-benzimidazole-4-yloxy)-propyl)diethyl-amine

HRID 17646Notes

Reaction equation

HRID 17646 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]([NH2:48])=[C:26]([O:39][CH2:40][CH2:41][CH2:42][N:43]([CH2:46][CH3:47])[CH2:44][CH3:45])[CH:27]=[C:28]([O:30][CH2:31][CH2:32][CH2:33][N:34]([CH2:37][CH3:38])[CH2:35][CH3:36])[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][CH2:33][N:34]([CH2:35][CH3:36])[CH2:37][CH3:38])[CH:27]=[C:26]([O:39][CH2:40][CH2:41][CH2:42][N:43]([CH2:46][CH3:47])[CH2:44][CH3:45])[C:25]=2[N:48]=[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 669775442-Butylamino-4,6-di(3-diethylaminopropoxy)anilineHCID 713506694-[2-(4-Chlorophenyl)ethoxy]benzaldehyde

Product 1

HCID 59699247(3-(1-Butyl-2-{4-[2-(4-chlorophenyl)-ethoxy]-phenyl}-6-(3-diethylaminopropoxy)-1h-benzimidazole-4-yloxy)-propyl)diethyl-amineYield 31.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

This compound was prepared according to General Procedure K by refluxing a mixture of 4-[2-(4-chloro-phenyl)-ethoxy]-bezaldehyde (300 mg) and N1-Butyl-3,5-bis-(3-diethylamino-propoxy)-benzene-1,2-diamine (synthesized via General Procedures J1 and J2 and I) (200 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 (3-(1-Butyl-2-{4-[2-(4-chlorophenyl)-ethoxy]-phenyl}-6-(3-diethylaminopropoxy)-1H-benzimidazole-4-yloxy)-propyl)diethyl-amine (100 mg).

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-14efbab72da24eedbf5288a49371f785
Source dataset
uspto-grants-2010_06
Patent number
US07737285B2

Reaction notes

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