1-(4-Nitrobenzyl)piperidine → 4-(Piperidin-1-ylmethyl)aniline

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Reaction Steps

1-(4-Nitro-benzyl)-piperidine (0.089 g, 0.404 mmol) is dissolved in MeOH (5 mL), and to this solution is added 10% Pd/C (0.009 g, 0.404 mmol). The reaction mixture is stirred under an atmosphere of H2 for 18 h. The resulting mixture is filtered through celite, and the filtered catalyst is washed with excess EtOAc. The filtrate is concentrated under high vacuum to afford the product as a solid (0.076 g, 99%); 1H NMR (DMSO-d6) δ 1.29-1.40 (m, 2H), 1.40-1.51 (m, 4H), 2.17-2.30 (m, 4H), 3.18 (s, 2H), 4.88 (s, 2H), 6.46 (d, J=8.4 Hz, 2H), 6.87 (d, J=8.4 Hz, 2H); mass spectrum [(+) ESI], m/z 191 (M+H)+.

Provenance & Evidence