Water → Dimethyl(4-(3-pvridyloxy)butyl)amine Hemigalactarate

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Reaction Steps

To a solution of dimethyl(4-(3-pyridyloxy))butylamine (1.26 g, 6.49 mmol) in ethanol (10 mL) was added galactaric acid (0.682 g, 3.25 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 16 h. Very few solids precipitated. Consequently, the solution was concentrated, and the residue was slurried in ether. The solids were filtered, washed with ether and vacuum dried at 40° C. to give 1.06 g (54.7%) of a light-brown, flaky powder, mp 127-130° C. The compound exhibits a Ki of 3410 nM. The compound exhibits neurotransmitter release of 24 percent.

Provenance & Evidence