Water → 4-(3-Pyridyloxy)butylamine Hemigalactarate

To a solution of 4-(3-pyridyloxy)butylamine (1.25 g, 7.50 mmol) in ethanol (12 mL) was added galactaric acid (0.791 g, 3.76 mmol). Water (3 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) (4 mL). The filtrate was diluted with ethanol (30 mL). The mixture was allowed to cool to ambient temperature and was further cooled at 5° C. for 48 h. Very few solids precipitated. Consequently, the solution was concentrated to a flaky solid. The product was slurried in 2-propanol, and the 2-propanol was decanted. The product was vacuum dried at 40° C. to give 1.28 g (62.7%) of fine, white powder, mp 177-180° C. The compound exhibits a Ki of 232 nM; the effect at muscle sites is 0 percent; and the effect at ganglia sites is 11 percent. The compound exhibits neurotransmitter release of 100 percent.