1-Benzyl-4-(aminomethyl)piperidine (I) was protected at the primary amino group as the Boc derivative (II) and the N-benzyl group was subsequently removed by transfer hydrogenolysis with hydrazine and Pd/C to give piperidine (III). Alkylation of (III) with N-(5-bromopentyl)phthalimide (IV) afforded (V), which was subjected to hydrazinolysis of the phthalimido group, yielding primary amine (VI). Coupling of (VI) with 1-methylindole-3-carboxylic acid (VII) by means of EDC and HOBt gave rise to amide (VIII). The Boc protecting group of (VIII) was then cleaved by acidic treatment to furnish amine (IX). Finally, coupling of (IX) with 4-amino-5-chloro-2-methoxybenzoic acid (X) provided the title benzamide.

1-Benzyl-4-(aminomethyl)piperidine (I) was protected at the primary amino group as the Boc derivative (II) and the N-benzyl group was subsequently removed by transfer hydrogenolysis with hydrazine and Pd/C to give piperidine (III). Alkylation of (III) with N-(5-bromopentyl)phthalimide (IV) afforded (V), which was subjected to hydrazinolysis of the phthalimido group, yielding primary amine (VI). Coupling of (VI) with 1-methylindole-3-carboxylic acid (VII) by means of EDC and HOBt gave rise to amide (VIII). The Boc protecting group of (VIII) was then cleaved by acidic treatment to furnish amine (IX). Finally, coupling of (IX) with 4-amino-5-chloro-2-methoxybenzoic acid (X) provided the title benzamide.