4-[2-(3-nitrophenoxy)ethyl]morpholine → 3-(2-Morpholin-4-ylethoxy)aniline

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A mixture of 4-[2-(3-nitro-phenoxy)-ethyl]-morpholine (4.0 g, 13 mmol) and 5% Pd—C (0.3 g) in ethyl acetate (100 mL) was hydrogenated under 50 psi hydrogen for 23 hours. The mixture was filtered through Celite, and the filtrate was evaporated in vacuo, providing 3.0 g, in 86% yield; 1H NMR (CDCl3) δ 2.58 (t, J=4.7 Hz, 4H), 2.78 (t, J=5.8 Hz, 2H), 3.65 (br, 2H), 3.73 (t, J=4.7 Hz, 4H), 4.07 (t, J=5.8 Hz, 2H), 6.24-6.34 (m, 3H), 7.05 (t, J=8.1 Hz, 1H).

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