3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-5-nitro-1H-indole → 3-(1-Methylpiperidin-4-yl)-1h-indol-5-amine

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A mixture of 3-(1-methyl-1,2,5,6-tetrahydropyridin-4-yl)-5-nitro-1H-indole (D1, 2.00 g, 7.8 mmole) and 10% palladium on carbon (0.25 g) in methanol (50 ml) and DMF (50 ml) was shaken under an atmosphere of hydrogen at 50 psi/344.8 KPa for 18 hours. The mixture was filtered and evaporated to dryness. The residue was partitioned between dichloromethane (75 ml) and water (30 ml). The organic phase was separated, washed with brine, dried (Na2SO4) and evaporated to dryness. Trituration of the residue with diethyl ether afforded the title compound as pale brown solid (1.15 g).

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