Hydrochloric Acid → Octahydro-[1,4]dioxino[2,3-c]pyridine

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Reaction Steps

A mixture of tert-butyl hexahydro-[1,4]dioxino[2,3-c]pyridine-6(7H)-carboxylate (800 mg, 4.47 mmol, 1 eq) in a solution of HCl in MeOH (15 mL) was stirred for 1 h at room temperature and concentrated in vacuo to give octahydro-[1,4]dioxino[2,3-c]pyridine. A mixture of the above residue, 1-bromo-3-chloropropane (2.84 g, 8.17 mmol, 4 eq) and K2CO3 (2.46 mg, 17.80 mmol, 4 eq) in acetone (60 mL) was heated to reflux overnight, cooled to room temperature and filtered. The filtrate was concentrated in vacuo and the residue was purified by a silica gel column chromatography (20:1 (v/v) CH2Cl2/MeOH) to give the title compound as pale yellow oil (500 mg, 45.00%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 220.1 (M+1).

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