3-Cyanomethyl-4-chloro-5-benzyloxyindole → 3-(2-Aminoethyl)-4-chloro-5-benzyloxyindole

Participants

Reaction Steps

A solution of 3-cyanomethyl-4-chloro-5-benzyloxyindole (1.00 g, 3.37 mmol) in methanolic ammonia (30 ml) was hydrogenated over Raney nickel for 21/2 hours at room temperature, at 30 p.s.i. pressure. After filtering off the catalyst, the filtrate was evaporated to give 3-(2-aminoethyl)-4-chloro-5-benzyloxyindole as an oil (1.05 g, 100%). Part of this product (170 mg, 0.57 mmol) was treated with excess ethereal HCl, and the mixture was evaporated to dryness to leave a pink solid, which was recrystallised from ethanol/ether to give 3-(2-amino-ethyl)-4-chloro-5-benzyloxyindole hydrochloride (108 mg) m.p. 224°-5° C.

Provenance & Evidence