Hydrochloric Acid → 1H-Indole-5-methanamine, 2-(trifluoromethyl)-, hydrochloride (1:1)

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Reaction Conditions

Reaction Steps

2-(trifluoromethyl)-1H-indole-5-carbonitrile (Intermediate 3A, 25 g), PtO2.H2O (3%, 750 mg) and MeOH (175 mL) were added to a hydrogenation flask. 4M HCl in dioxane (89 mL) was added and the reaction vessel is purged with N2 and then H2. The mixture was hydrogenated at 60 psi of H2 and 17-23° C. for 24 hrs. The mixture was filtered through celite and then through a 0.2 μm PTFE filter. MP-TMT resin (15 wt %) was then added and the slurry was stirred for 3 hrs at 40° C., cooled to 17-23° C., and then filtered through a pad of celite. The celite pad and resin were washed with MeOH (100 mL). The solution was concentrated to a minimum by vacuum distillation and n-propanol (200 mL) was added and concentrated to a minimum. Toluene (200 mL) was added and then cyclohexane (75 mL) and the slurry was allowed to stir for 2 hrs at 17-23° C. The mixture was then cooled to 0-5° C. and allowed to stir for 2 hrs. The solid was filtered and washed with toluene to give the title compound (25.3 g);

Provenance & Evidence