4-[2-(4-Nitrophenoxy)ethyl]morpholine → 4-(2-Morpholinoethoxy)aniline

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A mixture of 4-[2-(4-nitro-phenoxy)-ethyl]-morpholine (3.2 g, 13 mmol) and 5% Pd—C (0.3 g) in ethyl acetate (70 mL) was hydrogenated under 50 psi hydrogen for 20 hours. The mixture was filtered through Celite, and the filtrate was evaporated in vacuo, providing 2.0 g, in 72% yield; 1H NMR (CDCl3) δ 2.57 (t, J=4.6 Hz, 4H), 2.77 (t, J=5.8 Hz, 2H), 3.74 (t, J=4.6 Hz, 4H), 4.04 (t, J=5.8 Hz, 2H), 6.63 (d, J=8.8 Hz, 2H), 6.75 (d, J=8.8 Hz, 2H).

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