Water → Ethyl(3-(3-pyridyloxy)propyl)amine Hemigalactarate

To a solution of ethyl(3-(3-pyridyloxy)propyl)amine (400 mg, 2.20 mmol) in ethanol (11 mL) was added galactaric acid (233 mg, 1.10 mmol). Water (3.5 mL) was added drop-wise, while warming the solution to reflux. To remove some white, insoluble solids, the warm solution was filtered through a glass wool plug, washing the filter plug with a warm solution of ethanol-water (4:1, v/v) (3.5 mL). The filtrate was diluted with ethanol (17 mL). The mixture was allowed to cool to ambient temperature and was further cooled at 5° C. Very few solids precipitated. Consequently, the solution was concentrated to a residue that was vacuum dried. The solids were slurried in 2-propanol, and the 2-propanol was evaporated. The resulting solids were slurried in anhydrous ether. The product was filtered, washed with ether, and vacuum dried at 40° C. to give 348 mg (55.0%) of a brown, flaky powder, mp 147-150° C. The compound exhibits a Ki of 66 nM; the effect at muscle sites is 13 percent; and the effect at ganglia sites is 13 percent. The compound exhibits neurotransmitter release of 57 percent.