Water → 2-(3-Pyridyloxy)ethylamine Hemigalactarate

Participants

Reaction Steps

To a solution of 2-(3-pyridyloxy)ethylamine (0.390 g, 2.823 mmol) in ethanol (6 mL) was added galactaric acid (0.276 g, 1.312 mmol). Water (1.7 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) (1.9 mL). The filtrate was diluted with ethanol (9 mL). The mixture was allowed to cool to ambient temperature and was further cooled at 5° C. for 12 days. The product had precipitated as a semi-crystalline oil. The solvent was removed by rotary evaporation, and the resulting solids were vacuum dried at 40° C. for 24 h. The resulting solids were slurried in 2-propanol, and subsequently diluted with anhydrous ether. The solids were filtered, washed with ether, and vacuum dried at 40° C. for 24 h to give 0.598 g (87.1%) of a fluffy, off-white powder, mp 151-156° C. The compound exhibits a Ki of 1600 nM. The compound exhibits neurotransmitter release of 30 percent.

Provenance & Evidence