Water → HCID 12112227, compound

To a solution of cyclopropyl(3-(3-pyridyloxy)propyl)amine (0.239 g, 1.244 mmol) in ethanol (4 mL) was added galactaric acid (130.7 mg, 622 mmol). Water (1.0 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) (1 mL). The filtrate was diluted with ethanol (6 mL), cooled to ambient temperature and kept at 5° C. for 24 h. Crystallization did not occur. Consequently, the solution was concentrated by rotary evaporation to a brown, glassy residue. The residue was dissolved in 2-propanol containing a few drops of water, and the solution was concentrated to a syrup. The syrup was slurried in a mixture of 2-propanol-diethyl ether, producing a somewhat powdery solid. The solvents were evaporated on a rotary evaporator, and the resulting solids were slurried in a mixture of 2-propanol-diethyl ether. The mixture was stored at 5° C. for 24 h. The solvent was decanted; the tan solids were washed with ether (3×5 mL), decanting the wash each time. The tan solids were dried under a stream of nitrogen and under high vacuum to give 0.246 g (66.5%) of a light-beige powder, mp 124-130° C. The compound exhibits a Ki of 165 nM; the effect at muscle sites is 9 percent; and the effect at ganglia sites is 10 percent. The compound exhibits neurotransmitter release of 51 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) (1 mL)
6. additionThe filtrate was diluted with ethanol (6 mL)
7. customCrystallization
8. concentrationConsequently, the solution was concentrated by rotary evaporation to a brown, glassy residue
9. dissolutionThe residue was dissolved in 2-propanol containing a few drops of water
10. concentrationthe solution was concentrated to a syrup
11. additionThe syrup was slurried in a mixture of 2-propanol-diethyl ether
12. customproducing a somewhat powdery solid
13. customThe solvents were evaporated on a rotary evaporator
14. additionthe resulting solids were slurried in a mixture of 2-propanol-diethyl ether
15. waitThe mixture was stored at 5° C. for 24 h
16. customThe solvent was decanted
17. washthe tan solids were washed with ether (3×5 mL)
18. customdecanting the
19. washwash each time
20. customThe tan solids were dried under a stream of nitrogen and under high vacuum

ORD record

ord-40805da22df145d5ad8625cd89ced662

Source dataset

uspto-grants-2002_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06441006B2