反应 #2320160

反应方程式

(2-morpholino-3-pyridinyl)methanol

thionyl chloride

→

(2-morpholino-3-pyridinyl)methylchloride

chloride

溶剂

dichloromethane

反应条件

后处理

1. 1
   其他the solvents were removed under reduced pressure
2. 2
   workup.DISSOLUTIONthe residue was dissolved
3. 3
   浓缩concentrated repeatedly in dichloromethane
4. 4
   其他to remove excess of thionyl chloride

实验过程

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)+;

来源