Allyl chloride → N-Allyl-2,2'-iminodiethanol

A one liter, 3-necked, round bottomed flask, equipped with mechanical stirrer, dry ice condenser, thermometer and addition funnel (mounted atop condenser), was charged with diethanolamine (210.3 g, 2.0 mol). Finely ground sodium carbonate (17 g, 1.1 mol) was added to the flask. The amine was heated and stirred at 80° and the sodium carbonate dissolved. Allyl chloride (168.3 g, 2.2 mol) was added dropwise while keeping the reflux rate low and the temperature between 100° and 110° C. for between 2 and 3 hours. Stirring was continued at about 100° for 12 hours. The reaction mixture was allowed to cool and then diluted with dichloromethane (500 mL). The reaction mixture was then filtered. The residual salts in the reaction vessel were slurried with dichloromethane and filtered and finally all the salts were rinsed again with dichloromethane. The solvent was evaporated under reduced pressure to yield N-allyldiethanolamine (297.7 g, 102%) as a clear yellow oil. After cooling there was additional salt precipitation although the weight recorded was 297 g. Gas chromatographic analysis indicated that the product was approximately 90% pure. Distillation of the nearly pure material was conducted using a simple distillation head. Product boiling between 96° and 100° at 0.05 mL was collected affording 238 g (82% of the pure product):