Water → Ethyl(3-(3-pyridyloxy)propyl)amine Hemigalactarate

To a solution of ethyl(3-(3-pyridyloxy)propyl)amine (400 mg, 2.20 mmol) in ethanol (11 mL) was added galactaric acid (233 mg, 1.10 mmol). Water (3.5 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) (3.5 mL). The filtrate was diluted with ethanol (17 mL). The mixture was allowed to cool to ambient temperature and was further cooled at 5° C. Very few solids precipitated. 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 348 mg (55.0%) of a brown, flaky powder, mp 147-150° C. The compound exhibits a Ki of 66 nM; the effect at muscle sites is 13 percent; and the effect at ganglia sites is 13 percent. The compound exhibits neurotransmitter release of 57 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 (17 mL)
7. temperaturewas further cooled at 5° C
8. customVery few solids precipitated
9. concentrationConsequently, the solution was concentrated to a residue that
10. customdried
11. customthe 2-propanol was evaporated
12. filtrationThe product was filtered
13. washwashed with ether, and vacuum
14. customdried at 40° C.
15. customto give 348 mg (55.0%) of a brown, flaky powder, mp 147-150° C

ORD record

ord-c67e7c7d1a91462aad38deafc1857a1f

Source dataset

uspto-grants-2002_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06441006B2