Water → (3-Benzo[3,4-d]1,3-dioxolan-5-yloxypropyl)methylamine Hemigalactarate

Participants

Reaction Steps

To a solution of (3-benzo[3,4-d]1,3-dioxolan-5-yloxypropyl)methylamine (0.252 g, 1.21 mmol) in ethanol (6 mL) was added galactaric acid (140.0 mg, 0.67 mmol). Water (1.5 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) (1.5 mL). The filtrate was diluted with ethanol (7.5 mL). The mixture was allowed to cool to ambient temperature and was further cooled at 5° C. for 48 h. The precipitate was filtered, washed with ether, and vacuum dried at 40° C. for 16 h to give 301 mg (79.4%) of a white, crystalline solid, mp 158-160° C. The compound exhibits a Ki of 16600 nM. The compound exhibits neurotransmitter release of 41 percent.

Provenance & Evidence