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

Participants

Reaction Steps

To a solution of 4-[2-(4-nitro-phenoxy)-ethyl]-morpholine (2.25 g, 8.93 mmol) in ethanol (40 mL) is added palladium hydroxide (0.313 g, 0.45 mmol) and the mixture is stirred in a Parr-apparatus under hydrogen pressure (5 bars) for 2 hours. Filtration over Celite 521 and evaporation gave a red oil purified by silica gel column chromatography. Elution with DCM and a mixture 90:10 DCM:MeOH affords the title compound as a white solid (1.256 g, 63%). 1H-NMR (400 MHz, CDCl3) δ (ppm) 2.52-2.63 (4H, m), 2.71-2.80 (2H, t), 3.46 (2H, br s), 3.70-3.78 (4H, m), 4.00-4.10 (2H, m), 6.65 (2H, d), 6.77 (2H, d).

Provenance & Evidence