Water → Methyl(3-(5-(phenylmethoxy)(3-pyridyloxy))propyl)amine Hemigalactarate

To a solution of methyl(3-(5-(phenylmethoxy)(3-pyridyloxy))propyl)amine (1.07 g, 3.929 mmol) in ethanol (15 mL) was added galactaric acid (0.413 g, 1.964 mmol). Water (1.5 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) (5 mL). The filtrate was diluted with ethanol (23 mL). The mixture was allowed to cool to ambient temperature; however, no solids precipitated. The solution was concentrated by rotary evaporation and briefly dried under high vacuum. The resulting brown solids were dissolved in a mixture of hot 2-propanol (˜15 mL) and water (0.8 mL); the dark-brown solution was allowed to cool to ambient temperature. After 30 min of precipitation, the batch was diluted with 2-propanol (30 mL) and stored at 5° C. for 16 h. The resulting solids were filtered, washed with cold 2-propanol (3×5 mL) and vacuum dried at 45° C. to give 0.967 g (65.2%) of a beige powder, mp 137-140° C. The compound exhibits a Ki of 2 nM; the effect at muscle sites is 1 percent; and the effect at ganglia sites is 3 percent. The compound exhibits neurotransmitter release of 38 percent.