Acetic Acid → (1H-benzimidazol-2-yl)-[1-(4-phenyl-butyl)-piperidin-4-ylmethyl]-amine

HRID 2109990Notes

Reaction equation

HRID 2109990 reaction equation
[C:1](O)(=O)[CH3:2].C(O[BH-](O[C:15](=O)[CH3:16])OC(=O)C)(=O)C.[Na+].[NH:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[N:21]=[C:20]1[NH:28][CH2:29][CH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.Cl[CH:37](Cl)[CH3:38]>CN(C)C=O>[NH:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[N:21]=[C:20]1[NH:28][CH2:29][CH:30]1[CH2:35][CH2:34][N:33]([CH2:27][CH2:22][CH2:23][CH2:24][C:1]2[CH:2]=[CH:16][CH:15]=[CH:38][CH:37]=2)[CH2:32][CH2:31]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 63651,1-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 11481631N-(Piperidin-4-ylmethyl)-1H-benzo[d]imidazol-2-amine

Product 1

HCID 10193766(1H-benzimidazol-2-yl)-[1-(4-phenyl-butyl)-piperidin-4-ylmethyl]-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After adding acetic acid (28.6 μl) and sodium triacetoxyborohydride (52.99 mg, 0.25 mmol) to a mixed solution of (1H-benzimidazol-2-yl)-piperidin-4-ylmethyl-amine (30.32 mg, 0.10 mmol) and a mixed solution of the obtained 4-phenylbutylaldehyde (38.45 mg) in dichloroethane (1.0 ml) and dimethylformamide (0.5 ml), the mixture was stirred at room temperature overnight. The reaction suspension was passed through SCX (Bond Elute SCX500MG), and the SCX was washed with a mixed solution of chloroform-methanol (1:1). This was followed by elution with a 2N ammonia-methanol solution, and the solvent was then distilled off under reduced pressure to obtain a residue. The residue was purified by preparative HPLC to obtain (1H-benzimidazol-2-yl)-[1-(4-phenyl-butyl)-piperidin-4-ylmethyl]-amine. The compound was identified by LC-MS.

Workup

  1. washThe reaction suspension was passed through SCX (Bond Elute SCX500MG)
  2. washthe SCX was washed with a mixed solution of chloroform-methanol (1:1)
  3. washThis was followed by elution with a 2N ammonia-methanol solution
  4. distillationthe solvent was then distilled off under reduced pressure
  5. customto obtain a residue
  6. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-5a9db8e9cdce449097667333f0ec92ef
Source dataset
uspto-grants-2009_04
Patent number
US07517875B2

Reaction notes

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