1-[2-(3-Methoxy-4-nitro-phenoxy)-ethyl]-piperidine → 2-Methoxy-4-[2-(piperidin-1-yl)ethoxy]aniline

Participants

Reaction Steps

A mixture of 1-[2-(3-methoxy-4-nitro-phenoxy)-ethyl]-piperidine (1.5 g, 5.4 mmol) and 5% Pd—C (0.5 g) in ethyl acetate (70 mL) was shaken under 50 psi of hydrogen for 18 hours. The mixture was filtered through Celite and evaporated, providing 1.1 g of the product, in 81% yield: 1H NMR (DMSO-d6) δ 1.45-1.53 (m, 6H), 2.35-2.41 (m, 4H), 2.59 (t, J=6.0 Hz, 2H), 3.74 (s, 3H), 3.93 (t, J=6.0 Hz, 2H), 6.28 (dd, J=8.3 Hz, J=2.6 Hz, 1H), 6.45 (d, J=2.6 Hz, 1H), 6.63 (d, J=8.3 Hz, 1H).

Provenance & Evidence