4-(Aminomethyl)piperidine → Methyl 3-(3-cyanophenyl)-5-[(piperidin-4-ylmethyl)aminomethyl]benzoate

Participants

Reaction Steps

In 20 ml of toluene, were added 1.0 g of the compound obtained in Example 11 and 500 mg of 4-aminomethylpiperidine. The resulting mixture was refluxed using a Dean-Stark device under heating for 2 hours to remove the produced water. The solvent was then evaporated, and 20 ml of anhydrous methanol was added to dissolve the residue. To the obtained solution, was added 100 mg of 5% palladium-carbon. The mixture was stirred at room temperature under hydrogen atmosphere. After 4 hours, 200 mg of the 5% palladium-carbon was further added, and the reaction mixture was stirred for another 65 hours. The catalyst was separated by filtration, and the reaction mixture was concentrated. The resulting concentrate was then dissolved in a mixed solvent of water-dichloromethane, and the aqueous layer was separated and concentrated to afford 0.82 g (60%) of the title compound as a light-yellow oily substance.

Provenance & Evidence