Thionyl Chloride → N-(2-Chloroethyl)-N-methylbenzylamine hydrochloride

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The procedure of Hall, et al.[Organic Syntheses Coll. Vol. 4, 1963, 333-335] was used. To thionyl chloride (22.92 mL, 03.14 mol) at 0° C. was added dropwise N-benzyl-N-methyl ethanolamine (50 g, 0.303 mol). The creamy, off-white material was stirred for 1 hour at 0° C. and then 1 hour at room temperature. Anhydrous ethanol (129 mL) was added to the material. The solution was refluxed for 20 minutes and then was concentrated to an off-white solid. The solid was triturated with Et2O to give the title compound as a white solid (62.51 g, 94% yield, mp 136-138° C.).

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