Hydrochloric Acid → 8-Morpholino-2,3-dihydrobenzo[b][1,4]dioxin-5-amine

Participants

Reaction Steps

To a solution of N-(8-morpholino-2,3-dihydrobenzo[b][1,4]dioxin-5-yl)acetamide (2 g, 7.19 mmol) in methanol (100 mL) was added concentrated Hydrochloric acid (5 mL) and then the mixture was stirred at room temperature overnight. After the solvent was removed under reduce pressure, water was added and the pH was adjusted to 7-8 using aqueous sodium bicarbonate. The mixture was extracted with ethyl acetate and the combined organic phases were dried over anhydrous sodium sulfate, concentrated to give a crude product, which was purified by silica gel column chromatography (petroleum ether/ethyl acetate 2/1) to afford the product 8-morpholino-2,3-dihydrobenzo[b][1,4]dioxin-5-amine (1 g, yield 60%). 1H NMR (400 MHz, CDCl3) δ ppm 6.38-6.41 (d, 1H, J=8.4 Hz), 6.27-6.29 (d, 1H, J=8.4 Hz), 4.28-4.32 (m, 4H), 3.85-3.88 (t, 4H, J=4.8 Hz), 3.55 (s, 2H), 2.95-2.97 (t, 4H, J=4.8 Hz).

Provenance & Evidence