Hydrochloric Acid → HCID 57485786, compound

To a suspension of 4-(3-pyridinyl)-6-azabicyclo[3.2.1]oct-3-ene dihydrochloride (90 mg, 0.35 mmol) in 15 mL of dichloromethane was added a solution of formaldehyde (37% aqueous, 0.15 mL, ˜1.8 mmol). With vigorous stirring, solid sodium triacetoxyborohydride (300 mg, 1.4 mmol) was added in two portions. The reaction was allowed to stir overnight at ambient temperature. The reaction mixture was quenched by the addition of a sodium hydroxide solution (10% aqueous, approximately 1 mL), and the whole extracted with dichloromethane (2×10 mL). The organic extracts were washed successively with water and brine (10 mL each), and dried over sodium sulfate. Filtration and removal of solvent in vacuo gave a residue, which was dissolved in a small volume of methanol and treated with approximately 1 mL of 4M HCl in dioxane. The resulting solution was concentrated in vacua, and the residue taken up in a minimum amount of warm isopropanol. After cooling briefly, ether was added to the point of cloudiness, and the solution cooled slowly to ambient temperature. A sticky solid precipitate formed which resisted crystallization. Solvents were removed in vacuo, leaving the product as a hygroscopic, gummy mass (30 mg, 32%).

1. customThe reaction mixture was quenched by the addition of a sodium hydroxide solution (10% aqueous, approximately 1 mL)
2. extractionthe whole extracted with dichloromethane (2×10 mL)
3. washThe organic extracts were washed successively with water and brine (10 mL each)
4. dry with materialdried over sodium sulfate
5. filtrationFiltration and removal of solvent in vacuo
6. customgave a residue, which
7. concentrationThe resulting solution was concentrated in vacua
8. temperatureAfter cooling briefly
9. additionether was added to the point of cloudiness
10. temperaturethe solution cooled slowly to ambient temperature
11. customA sticky solid precipitate formed which
12. customcrystallization
13. customSolvents were removed in vacuo
14. customleaving the product as a hygroscopic, gummy mass (30 mg, 32%)

ORD record

ord-43afd99be1d243e2951c313f7234e138

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07402592B2