1-BOC-4-[2-(4-amino-3-butylamino-phenoxy)-ethyl]-piperazine → 1-butyl-2-(4-[2-(4-chlorophenyl)ethoxy]-phenyl)-6-(2-piperazin-1-yl-ethoxy)-1H-benzimidazole

HRID 17645Notes

Reaction equation

HRID 17645 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.C([N:26]1[CH2:31][CH2:30][N:29]([CH2:32][CH2:33][O:34][C:35]2[CH:40]=[CH:39][C:38]([NH2:41])=[C:37]([NH:42][CH2:43][CH2:44][CH2:45][CH3:46])[CH:36]=2)[CH2:28][CH2:27]1)(OC(C)(C)C)=O>>[CH2:43]([N:42]1[C:37]2[CH:36]=[C:35]([O:34][CH2:33][CH2:32][N:29]3[CH2:28][CH2:27][NH:26][CH2:31][CH2:30]3)[CH:40]=[CH:39][C:38]=2[N:41]=[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)[CH2:44][CH2:45][CH3:46]

Participants

3

Reactant 2

HCID 669776661-BOC-4-[2-(4-amino-3-butylamino-phenoxy)-ethyl]-piperazineHCID 713506694-[2-(4-Chlorophenyl)ethoxy]benzaldehyde

Product 1

HCID 596991461-butyl-2-(4-[2-(4-chlorophenyl)ethoxy]-phenyl)-6-(2-piperazin-1-yl-ethoxy)-1H-benzimidazoleYield 59.6%

Procedure

A mixture of 4-[2-(4-chloro-phenyl)-ethoxy]-benzaldehyde (0.08 g)and 1-BOC-4-[2-(4-amino-3-butylamino-phenoxy)-ethyl]-piperazine (0.10 g) was subjected to General Procedure K. Ethanol was removed in vacuo and the residue purified on silica gel with 1-2% MeOH/DCM. The BOC-group was removed employing General Procedure T1 to give 1-butyl-2-{4-[2-(4-chlorophenyl)ethoxy]-phenyl}-6-(2-piperazin-1-yl-ethoxy)-1H-benzimidazole (0.081 g).

Workup

  1. customEthanol was removed in vacuo
  2. customthe residue purified on silica gel with 1-2% MeOH/DCM
  3. customThe BOC-group was removed

Sources & evidence

ORD record
ord-eca42764dd114ce49ad583c5931465c2
Source dataset
uspto-grants-2010_06
Patent number
US07737285B2

Reaction notes

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