Toluene → Tert-butyl 4-(3-(4-amino-5-chloro-2-methylphenoxy)propyl)piperazine-1-carboxylate

Participants

Reaction Steps

A flask was charged with tert-butyl 4-(3-(5-chloro-2-methyl-4-nitrophenoxy)propyl)-piperazine-1-carboxylate (1.2 g, 2.9 mmol), ammonium formate (0.84 g, 13 mmol), and iron powder (0.74 g, 13 mmol). Toluene (20 mL) and water (20 mL) were added to the flask and the mixture was heated to reflux for 6 hours, after which time, the mixture was filtered through a plug of Celite. The supernatant was extracted with ethyl acetate and water. The organic solvent was removed on a rotary evaporator under reduced pressure to yield tert-butyl 4-(3-(4-amino-5-chloro-2-methylphenoxy)propyl)piperazine-1-carboxylate as a brown oil (0.99 g, 89% yield). 1H-NMR (400 MHz, DMSO-d6): δ 6.77 (s, 1H), 6.61 (s, 1H), 4.76 (s, 2H), 3.86 (t, 6.1 Hz, 2H), 3.30 (s, br, 4H), 2.50 (m, 2H), 2.31 (m, 2H), 2.03 (s, 3H), 1.82 (m, 2H), 1.39 (s, 9H). MS (EI): 384 (MH+).

Provenance & Evidence