Benzaldehyde → HCID 58306549, compound

Participants

Reaction Steps

To a mixture of methyl 4-[(1S)-1-({[1-(piperidin-4-ylmethyl)-1H-indol-7-yl]carbonyl}amino)ethyl]benzoate hydrochloride (150 mg) and dichloromethane (2.0 mL) were added sodium triacetoxyborohydride (210 mg) and benzaldehyde (70 mg) at room temperature, followed by stirring for 3 days. To the reaction mixture was added water. In addition, the mixture was alkalified by adding a 1 M aqueous sodium hydroxide solution and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to obtain methyl 4-{(1S)-1-[({1-[(1-benzyl piperidin-4-yl)methyl]-1H-indol-7-yl}carbonyl)amino]ethyl}benzoate (121 mg) as a white solid.

Provenance & Evidence