3-(3-Tert-butylphenoxy)benzaldehyde → 1-butyl-2-{3-[3-tert-butyl-phenoxy]-phenyl}-6-(2-piperazin-1-yl-ethoxy)-1H-benzimidazole

HRID 901636Notes

Reaction equation

HRID 901636 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[C:19]([NH:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:18]=2)[CH2:10][CH2:9]1)(OC(C)(C)C)=O.[C:29]([C:33]1[CH:34]=[C:35]([CH:45]=[CH:46][CH:47]=1)[O:36][C:37]1[CH:38]=[C:39]([CH:42]=[CH:43][CH:44]=1)[CH:40]=O)([CH3:32])([CH3:31])[CH3:30]>>[CH2:25]([N:24]1[C:19]2[CH:18]=[C:17]([O:16][CH2:15][CH2:14][N:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[CH:22]=[CH:21][C:20]=2[N:23]=[C:40]1[C:39]1[CH:42]=[CH:43][CH:44]=[C:37]([O:36][C:35]2[CH:45]=[CH:46][CH:47]=[C:33]([C:29]([CH3:32])([CH3:31])[CH3:30])[CH:34]=2)[CH:38]=1)[CH2:26][CH2:27][CH3:28]

Participants

3

Reactant 2

HCID 639434473-(3-Tert-butylphenoxy)benzaldehydeHCID 669776661-BOC-4-[2-(4-amino-3-butylamino-phenoxy)-ethyl]-piperazine

Product 1

HCID 596991641-butyl-2-{3-[3-tert-butyl-phenoxy]-phenyl}-6-(2-piperazin-1-yl-ethoxy)-1H-benzimidazole

Procedure

A mixture of 1-BOC-4-[2-(4-amino-3-butylamino-phenoxy)-ethyl]-piperazine (synthesized via General Procedures G1 and G2 and H) (0.130 g, 0.512 mmol) and 3-(3-tert-butylphenoxy) benzaldehyde was subjected to General Procedure K. Reaction was concentrated and purified on silica gel chromatography using DCM-2% MeOH/DCM. The BOC-group was removed employing General Procedure T1 to give 1-butyl-2-{3-[3-tert-butyl-phenoxy]-phenyl}-6-(2-piperazin-1-yl-ethoxy)-1H-benzimidazole (0.10 g).

Workup

  1. customReaction
  2. concentrationwas concentrated
  3. custompurified on silica gel chromatography
  4. customThe BOC-group was removed

Sources & evidence

ORD record
ord-1500f88990d448d3b6ed6d2301e4bfca
Source dataset
uspto-grants-2008_04
Patent number
US07361678B2

Reaction notes

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