Water → HCID 12112227, compound

Participants

Reaction Steps

To a solution of cyclopropyl(3-(3-pyridyloxy)propyl)amine (0.239 g, 1.244 mmol) in ethanol (4 mL) was added galactaric acid (130.7 mg, 622 mmol). Water (1.0 mL) was added drop-wise, while warming the solution to near reflux. To remove some white, insoluble crystals, 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 mL). The filtrate was diluted with ethanol (6 mL), cooled to ambient temperature and kept at 5° C. for 24 h. Crystallization did not occur. Consequently, the solution was concentrated by rotary evaporation to a brown, glassy residue. The residue was dissolved in 2-propanol containing a few drops of water, and the solution was concentrated to a syrup. The syrup was slurried in a mixture of 2-propanol-diethyl ether, producing a somewhat powdery solid. The solvents were evaporated on a rotary evaporator, and the resulting solids were slurried in a mixture of 2-propanol-diethyl ether. The mixture was stored at 5° C. for 24 h. The solvent was decanted; the tan solids were washed with ether (3×5 mL), decanting the wash each time. The tan solids were dried under a stream of nitrogen and under high vacuum to give 0.246 g (66.5%) of a light-beige powder, mp 124-130° C. The compound exhibits a Ki of 165 nM; the effect at muscle sites is 9 percent; and the effect at ganglia sites is 10 percent. The compound exhibits neurotransmitter release of 51 percent.

Provenance & Evidence