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 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. 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