The compound can be prepared by two related ways. Coupling of N-Boc-L-tryptophan (I) with benzyl methyl amine (II) employing EDC and HOBt afforded amide (III). The Boc of (III) group was removed by treatment with trifluoroacetic acid and anisole to give amine (IV). Then, sequential reaction of (IV) with 1,1'-carbonyldiimidazole and with piperidine (V) yielded the target urea. In a related procedure, urea formation between L-tryptophan benzyl ester (VI) and piperidine (V) gave (VII). Subsequent catalytic hydrogenolysis of the benzyl ester of (VII) provided acid (VIII). This was finally coupled to benzyl methyl amine (II) to produce the title compound.
The compound can be prepared by two related ways. Coupling of N-Boc-L-tryptophan (I) with benzyl methyl amine (II) employing EDC and HOBt afforded amide (III). The Boc group of (III) was removed by treatment with trifluoroacetic acid and anisole to give amine (IV). Then, sequential reaction of (IV) with 1,1'-carbonyldiimidazole and with piperidine (V) yielded the target urea. In a related procedure, urea formation between L-tryptophan benzyl ester (VI) and piperidine (V) gave (VII). Subsequent catalytic hydrogenolysis of the benzyl ester of (VII) provided acid (VIII). This was finally coupled to benzyl methyl amine (II) to produce the title compound.