3-(3-Hydroxypropyl)-1H-indole-5-carbonitrile → 5-(Aminomethyl)-1H-indole-3-propanol

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Reaction Steps

To a solution of 5-cyano-3-(3-hydroxypropyl)indole (1.00 g, 0.005 mol) in 30 mL of absolute ethanol was added 10% palladium-on-charcoal (1.00 g) and the mixture was hydrogenated on a Parr shaker at 40 psi for 6 h. The mixture was then filtered, through Celite, the filtercake was washed with additional ethanol and the filtrate was evaporated to give a colourless gum. Flash chromatography (SiO2 /MeCN-MeOH, 9:1 then MeCN-MeOH-NH4OH, 90:9:1) afforded the essentially pure title compound (0.67 g, 70%) as a colourless gum: IR (neat) 3250 cm-1 ; 1H NMR (DMSO-d6, 200 MHz) δ10.60 (s, 1H) , 7.41 (s, 1H), 7.23 (d, J=8.2 Hz, 1H), 7.04 (s, 1H), 7.02 (d, J=8.1 Hz, 1H), 4.4 (br s, 1H), 3.75 (s, 2H), 3.46 (t, J=6.5 Hz, 2H), 3.3 (br s, 2H), 2.68 (m, 2H), 1.78 (m, 2H).

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