Water → 2-(3-Pyridyloxy)ethylamine Hemigalactarate

To a solution of 2-(3-pyridyloxy)ethylamine (0.390 g, 2.823 mmol) in ethanol (6 mL) was added galactaric acid (0.276 g, 1.312 mmol). Water (1.7 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) (1.9 mL). The filtrate was diluted with ethanol (9 mL). The mixture was allowed to cool to ambient temperature and was further cooled at 5° C. for 12 days. The product had precipitated as a semi-crystalline oil. The solvent was removed by rotary evaporation, and the resulting solids were vacuum dried at 40° C. for 24 h. The resulting solids were slurried in 2-propanol, and subsequently diluted with anhydrous ether. The solids were filtered, washed with ether, and vacuum dried at 40° C. for 24 h to give 0.598 g (87.1%) of a fluffy, off-white powder, mp 151-156° C. The compound exhibits a Ki of 1600 nM. The compound exhibits neurotransmitter release of 30 percent.

1. temperaturewhile warming the solution
2. temperatureto reflux
3. customTo remove some white, insoluble solids
4. filtrationthe warm solution was filtered through a glass wool plug
5. washwashing the filter plug with a warm solution of ethanol-water (4:1
6. additionThe filtrate was diluted with ethanol (9 mL)
7. temperaturewas further cooled at 5° C. for 12 days
8. customThe product had precipitated as a semi-crystalline oil
9. customThe solvent was removed by rotary evaporation
10. customdried at 40° C. for 24 h
11. additionsubsequently diluted with anhydrous ether
12. filtrationThe solids were filtered
13. washwashed with ether, and vacuum
14. customdried at 40° C. for 24 h
15. customto give 0.598 g (87.1%) of a fluffy, off-white powder, mp 151-156° C

ORD record

ord-a4f4d5c468f1450a9ef879aaf4ca6cac

Source dataset

uspto-grants-2002_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06441006B2