Water → HCID 12112221, compound

Participants

Reaction Steps

To a solution of 3-(5-chloro-3-pyridyloxy)propylamine (1.00 g, 5.38 mmol) in ethanol (12 mL) was added galactaric acid (0.564 g, 2.688 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 (80 mL). The mixture was allowed to cool to ambient temperature and was further cooled at 5° C. for 48 h. No solids had formed. 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 0.996 g (63.5%) of a brown, flaky powder, mp 170-173° C. The compound exhibits a Ki of 46 nM; the effect at muscle sites is 0 percent; and the effect at ganglia sites is 4 percent. The compound exhibits neurotransmitter release of 110 percent.

Provenance & Evidence