Formic Acid → 3-Methyl-7-(3-pyridinyl)-3-azabicyclo[3.3.1]non-6-ene dihydrochloride

7-(3-pyridinyl)-3-azabicyclo[3.3.1]non-6-ene dihydrochloride (90 mg, 0.33 mmol) was dissolved in 37% aqueous formaldehyde (3 ml), and 98% formic acid (10 ml) was added. This mixture was refluxed for 1 h. The reaction was then cooled, concentrated by rotary evaporation, and treated with saturated sodium bicarbonate solution (15 ml). It was then extracted with chloroform (3×15 ml), and the extracts were dried over sodium sulfate, filtered and concentrated by rotary evaporation. Concentrated HCl (5 drops) was added to a solution of the free base in ethanol (10 ml). The excess HCl and residual water were removed by repeated azeotropic rotary evaporation with ethanol. 3-Methyl-7-(3-pyridinyl)-3-azabicyclo[3.3.1]non-6-ene dihydrochloride was isolated as a white, hygroscopic solid (116 mg, >100% due to moisture content).

1. temperatureThis mixture was refluxed for 1 h
2. temperatureThe reaction was then cooled
3. concentrationconcentrated by rotary evaporation
4. additiontreated with saturated sodium bicarbonate solution (15 ml)
5. extractionIt was then extracted with chloroform (3×15 ml)
6. dry with materialthe extracts were dried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated by rotary evaporation
9. additionConcentrated HCl (5 drops) was added to a solution of the free base in ethanol (10 ml)
10. customThe excess HCl and residual water were removed
11. customrotary evaporation with ethanol

ORD record

ord-6314e34496c44fb5817866ff021f1dd3

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07402592B2