Quaternization of 5-aminoisoquinoline (I) in acetone afforded isoquinolinium salt (II), which was reduced with NaBH4 to the tetrahydroisoquinoline (III). Alternatively, 5-nitroisoquinoline (IV) was quaternized to give (V) and subsequently reduced with NaBH4 to afford 2-methyl-5-nitro-1,2,3,4-tetrahydroisoquinoline (VI), which was further reduced to amine (III) by catalytic hydrogenation over Pd/C. Amine (III) was finally coupled with acid chloride (VII) in the presence of Et3N to provide the title benzamide).