Thionyl Chloride → 4-(3-Chloropropyl)pyridine

Participants

Reaction Steps

To a stirred solution of 3-(4-pyridyl)propanol (22.05 g, 0.16 mol) in 100 mL of dry chloroform (CHCl3) at 0° C. was added dropwise a CHCl3 solution of thionylchloride (SOCl2, 17.5 mL, 0.24 mol). The reaction was allowed to warm to room temperature, stirred for 1 hour, and then brought to reflux for 1 hour. After cooling the reaction to room temperature, it was stripped of all solvent under reduced pressure and the residue was partitioned between CH2Cl2 and water that had been made basic with concentrated NH4OH. The aqueous phase was washed 2x with CH2Cl2 and the combined organic phase was dried (Na2SO4), filtered, and stripped of solvent to yield 24 g of crude product. This material was vacuum distilled at 68°-71° C. (0.3 mm) to give 24 g of the title compound.

Provenance & Evidence