Water → HCID 12112231, compound

Participants

Reaction Steps

To a solution of (3-(3-aminophenoxy)propyl)methylamine (2.77 g, 15.30 mmol) in ethanol was added galactaric acid (1.61 g, 7.65 mmol). Water 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). The filtrate was diluted with ethanol. The mixture was allowed to cool to ambient temperature and was further cooled at 5° C. 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 3.928 g (89.6%) of brown, powdery crystals, mp 160-170° C. The compound exhibits a Ki of 64 nM; the effect at muscle sites is 11 percent; and the effect at ganglia sites is 5 percent. The compound exhibits neurotransmitter release of 30 percent. The compound exhibits neurotransmitter release of 60 percent.

Provenance & Evidence