Thionyl Chloride → Chloride

Participants

Reaction Steps

To a solution of (2-morpholino-3-pyridinyl)methanol (1 g, 5.01 mmol)(purchased from Maybridge) in dichloromethane (20 ml) was added thionyl chloride (3 ml) dropwise at 0° C. and allowed to warm to room temperature. After stirring at room temperature for 6 hours, the solvents were removed under reduced pressure and the residue was dissolved and concentrated repeatedly in dichloromethane to remove excess of thionyl chloride. The obtained crude chloride intermediate, (2-morpholino-3-pyridinyl)methylchloride, was immediately dissolved in acetone (25 ml) and sodium azide (1.63 g, 25.05 mmol) was added at room temperature. The reaction was refluxed overnight, the solvents were removed under reduced pressure, dissolved in dichloromethane (25 ml) and washed with 1M NaHCO3 (25 ml). The aqueous layer was extracted with dichloromethane (2×20 ml). The combined organic extracts were dried (Na2SO4), filtered and concentrated to yield 0.62 g (57%) of product as a thick yellowish liquid. MS (ESI+) m/z 220 (M+H)+;

Provenance & Evidence