4-(3,4-Dinitrobenzyl)morpholine → 4-(Morpholinomethyl)benzene-1,2-diamine

Participants

Reaction Steps

4-(3,4-Dinitrobenzyl)morpholine (200 mg, 0.748 mmol) and 10% Pd/C (10 mg) were suspended in ethanol (10 mL) under nitrogen. The reaction mixture's atmosphere was exchanged for hydrogen and hydrogenation continued at ambient temperature and pressure for 24 h. The vessel was purged with nitrogen, and then the mixture was filtered through Celite with an ethanol (10 mL) rinsing. The solvent was removed in vacuo and purification by flash chromatography (5% CH3OH/CH2Cl2) afforded the title compound in a 65% yield. 1H NMR: (400 MHz, DMSO-d6): δ 6.46 (s, 1H), 6.40 (d, 1H, J=7.6 Hz), 6.27 (d, 1H, J=7.2 Hz), 4.37 (s, 2H), 4.32 (s, 2H), 3.52 (m, 4H), 3.18 (m, 4H), 2.26 (m, 4H).

Provenance & Evidence