Methanol → 2-[({1-[(3,5-Dichloro-2-hydroxyphenyl)methyl]4-fluoro-4-piperidyl}methyl)amino]benzimidazole-5-carboxylic acid methyl ester

Participants

Reaction Steps

After adding 3,5-dichloro-2-hydroxybenzaldehyde (57.3 mg, 0.3 mmol) and sodium triacetoxyborohydride (64 mg, 0.3 mmol) to a solution of 2-{[(4-fluoro-4-piperidyl)methyl]amino}benzimidazole-5-carboxylic acid methyl ester hydrochloride (30 mg, 0.1 mmol) in DMF-acetic acid (10:1) (1.0 ml), the mixture was stirred at room temperature overnight. Methanol (1.0 ml) was added to the reaction mixture to suspend the reaction, and after stirring for 1 hour, the solution was passed through SCX (Bond Elute SCX500MG: cationic ion-exchange resin, Varian). The SCX was washed with methanol and then with a mixed solution of chloroform/methanol (1/1), and elution was performed with a 0.5 N ammonia-dioxane solution to obtain 2-[({1-[(3,5-dichloro-2-hydroxyphenyl)methyl]4-fluoro-4-piperidyl}methyl)amino]benzimidazole-5-carboxylic acid methyl ester. The compound was identified by LC-MS.

Provenance & Evidence