2-[2-(4-Cyanophenyl)-ethyl]-1-methyl-benzimidazole-5-yl-carboxylic acid-(4-benzamido-piperidinyl)-amide → 2-[2-(4-Aminomethylphenyl)-ethyl]-1-methyl-benzimidazole-5-yl-carboxylic acid-(4-benzamido-piperidinyl)-amide

HRID 23912Notes

Reaction equation

HRID 23912 reaction equation
[C:1]([NH:9][CH:10]1[CH2:15][CH2:14][N:13]([NH:16][C:17]([C:19]2[CH:38]=[CH:37][C:22]3[N:23]([CH3:36])[C:24]([CH2:26][CH2:27][C:28]4[CH:33]=[CH:32][C:31]([C:34]#[N:35])=[CH:30][CH:29]=4)=[N:25][C:21]=3[CH:20]=2)=[O:18])[CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO>[C:1]([NH:9][CH:10]1[CH2:15][CH2:14][N:13]([NH:16][C:17]([C:19]2[CH:38]=[CH:37][C:22]3[N:23]([CH3:36])[C:24]([CH2:26][CH2:27][C:28]4[CH:33]=[CH:32][C:31]([CH2:34][NH2:35])=[CH:30][CH:29]=4)=[N:25][C:21]=3[CH:20]=2)=[O:18])[CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 225699282-[2-(4-Cyanophenyl)-ethyl]-1-methyl-benzimidazole-5-yl-carboxylic acid-(4-benzamido-piperidinyl)-amide

Product 1

HCID 697932822-[2-(4-Aminomethylphenyl)-ethyl]-1-methyl-benzimidazole-5-yl-carboxylic acid-(4-benzamido-piperidinyl)-amide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

2.0 g (4.1 mmol) 2-[2-(4-Cyanophenyl)-ethyl]-1-methyl-benzimidazole-5-yl-carboxylic acid-(4-benzamido-piperidinyl)-amide are hydrogenated in 30 ml of methanol in the presence of about 2 g of methanol-moist Raney Nickel at room temperature and standard pressure. The catalyst is filtered off and washed with methanol, and the solvent is distilled off under vacuum. The residue is hydrogenated over silica gel (acetic ester:methanol:ammonia, 80:20:1) and then chromatographed over an RP-18 column (gradient acetonitrile:water: 0-2 min. 90% water over 11 min. of 90 to 5% water, 5 min. 5% water). Yield: 0.4 g (20%); MPt.: 165-167° C.,

Workup

  1. filtrationThe catalyst is filtered off
  2. washwashed with methanol
  3. distillationthe solvent is distilled off under vacuum
  4. customchromatographed over an RP-18 column (gradient acetonitrile:water: 0-2 min. 90% water over 11 min. of 90 to 5% water, 5 min. 5% water)
  5. custom165-167° C.

Sources & evidence

ORD record
ord-cee7fc82ce7946779cc13ce232b639b0
Source dataset
uspto-grants-2005_02
Patent number
US06855713B2

Reaction notes

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