Water → HCID 131723462, compound

Participants

Reaction Steps

To a solution of methyl(3-(2-methyl(3-pyridyloxy))propyl)amine (1.19 g, 6.61 mmol) in ethanol (12 mL) was added galactaric acid (0.696 g, 3.30 mmol). Water (3 mL) was added dropwise, 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. No solids precipitated. Consequently, the solution was concentrated to a flaky solid. The solid was slurried in 2-propanol, filtered, washed with 2-propanol, and vacuum dried at 40° C. to give 1.37 g (72.8%) of an off-white, flaky powder, mp 145-148° C. The compound exhibits a Ki of 236 nM; the effect at muscle sites is 0 percent; and the effect at ganglia sites is 15 percent. The compound exhibits neurotransmitter release of 69 percent.

Provenance & Evidence