Water → HCID 12112223, compound

To a solution of methyl(3-(5-isopropoxy-3-pyridyloxy)propyl)amine (0.643 g, 2.87 mmol) in ethanol (10.7 mL) was added galactaric acid (302.0 mg, 1.44 mmol). Water (3.0 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) (3.4 mL). The filtrate was diluted with ethanol (16 mL), producing a white precipitate. 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 ethanol (10 mL), and vacuum dried at 40° C. for 24 h to give 251.1 mg (53.2%) of a white, crystalline solid, mp 118-120° C. The compound exhibits a Ki of 21 nM; the effect at muscle sites is 22 percent; and the effect at ganglia sites is 0 percent. The compound exhibits neurotransmitter release of 36 percent.

1. temperaturewhile warming the solution
2. temperatureto near reflux
3. customTo remove some white, insoluble crystals
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, v/v) (3.4 mL)
6. additionThe filtrate was diluted with ethanol (16 mL)
7. customproducing a white precipitate
8. temperaturewas further cooled at 5° C. for 48 h
9. filtrationThe precipitate was filtered
10. washwashed with ethanol (10 mL), and vacuum
11. customdried at 40° C. for 24 h
12. customto give 251.1 mg (53.2%) of a white, crystalline solid, mp 118-120° C

ORD record

ord-2960fd3a07024608b0a2b9efa39c442c

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06627648B1