4-AMINOMETHYLINDOLE

16136-52-0

3468-18-6

The general procedure for the synthesis of 4-(aminomethyl)indole from 4-cyanoindole was as follows:Preparation of C-(1H-indol-4-yl)-methylamine. At room temperature, 4-cyanoindole (7.5 g, 53 mmol) was dissolved in THF (100 ml) and then slowly added to 1.0 M lithium aluminum hydride solution in THF (100 ml). The reaction mixture was heated to reflux for 30 min and subsequently cooled to room temperature. After completion of the reaction, the reaction mixture was quenched with 1N NaOH solution and filtered. The filtrate was acidified with 1N HCl and stirred at room temperature for 10 minutes. Subsequently, the pH was adjusted to about 10, saturated NaHCO3 solution was added and extracted with n-butanol. The organic layer was separated and concentrated to dryness. The residue was ground with methanol, filtered to remove insoluble matter and the filtrate was concentrated under reduced pressure to give the target product. The final product was dried under high vacuum at 50 °C to give a white solid (7.27 g, 94% yield).