HCID 66977438, compound → HCID 59699235, compound

HRID 901641Notes

Reaction equation

HRID 901641 reaction equation
[CH2:1]([N:3]([CH2:26][CH3:27])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:15]=[C:14]([O:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)[CH:13]=[CH:12][C:9]=1[CH:10]=O)[CH3:2].[CH2:28]([NH:32][C:33]1[CH:39]=[C:38]([O:40][CH2:41][CH2:42][CH2:43][N:44]([CH2:47][CH3:48])[CH2:45][CH3:46])[CH:37]=[CH:36][C:34]=1[NH2:35])[CH2:29][CH2:30][CH3:31]>C(O)C>[CH2:28]([N:32]1[C:33]2[CH:39]=[C:38]([O:40][CH2:41][CH2:42][CH2:43][N:44]([CH2:47][CH3:48])[CH2:45][CH3:46])[CH:37]=[CH:36][C:34]=2[N:35]=[C:10]1[C:9]1[CH:12]=[CH:13][C:14]([O:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)=[CH:15][C:8]=1[O:7][CH2:6][CH2:5][CH2:4][N:3]([CH2:26][CH3:27])[CH2:1][CH3:2])[CH2:29][CH2:30][CH3:31]

Participants

4

Reactant 2

HCID 66977438HCID 66977438, compoundHCID 86591967HCID 86591967, compound

Product 1

HCID 59699235HCID 59699235, compoundYield 64.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(3-diethylaminopropoxy)-4-[2-(4-chlorophenyl)ethoxy]benzaldehyde (synthesized via General Procedures D1 and D2) (429 mg; 1.1 mmol) and 2-(n-butylamino)-4-(3-diethylaminopropoxy)aniline (synthesized via General Procedures G1 and G2 and I) (293 mg; 1 mmol) in ethanol (5 mL) was heated to reflux following General Procedure K. The crude product was purified by silica gel column chromatography using 10% MeOH in DCM with a gradual increment of triethylamine (0.2 to 1.0%) as eluent to afford of (3-{2-[1-butyl-6-(3-diethylamino-propoxy)-1H-benzimidazol-2-yl]-5-[2-(4-chloro-phenyl)-ethoxy]-phenoxy}-propyl)-diethylamine (430 mg).

Workup

  1. temperatureto reflux
  2. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ea6edb7178ab434b8ffe3461e46a8ec6
Source dataset
uspto-grants-2008_04
Patent number
US07361678B2

Reaction notes

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