Tert-butyl 4-(3-methyl-4-nitrophenoxy)piperidine-1-carboxylate → Tert-butyl 4-(3-methyl-4-aminophenoxy)piperidine-1-carboxylate

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Reaction Steps

tert-Butyl 4-(3-methyl-4-nitrophenoxy)piperidine-1-carboxylate (5.2 g, 14.30 mmoles) was dissolved in ethyl acetate (60 ml) and methanol (10 ml). The solution was treated with 500 mg of 10% palladium on carbon (50% water w/w). The slurry was then shaken on a Parr hydrogenator and treated with a 40 psi atmosphere of hydrogen gas, at room temperature. After 18 hours, the slurry was filtered through a plug of Celite, which was subsequently washed with ethyl acetate (50 ml) and methanol (50 ml). The resulting filtrate was then evaporated at reduced pressure and then triturated with hexane to give a solid. This material was filtered off and dried at reduced pressure to give 4.87 g of tert-butyl 4-(3-methyl-4-aminophenoxy)piperidine-1-carboxylate (100% yield). 1H-NMR (400 MHz, DMSO-d6) δ 6.33 (d, 1H), 6.32 (s, 1H), 6.23 (s, 1H), 5.85 (bs, 2H), 3.70 (m, 1H), 3.39 (m, 2H), 3.29 (m, 2H), 2.35 (s, 3H), 2.00 (m, 2H), 1.75 (m, 2H), 1.42 (s, 9H). MS (EI): for C18H28N2O3: 320 (MH+).

Provenance & Evidence