Triethylamine → 1-Azabicyclo[2.2.1]hept-4-yl-N-methoxy-N-methyl carboxamide

Ethyl-1-azabicyclo[2.2.1]hept-4-ylcarboxylate (D20, 1.75 g, 0.01 mole) in concentrated hydrochloric acid (50 ml) was heated under reflux for 1.5 h. The reaction was then concentrated in vacuo to give a solid which was dissolved in thionyl chloride (30 ml) and heated under reflux for 1.5 h. The mixture was then evaporated to dryness, and freed from residual thionyl chloride by co-evaporation which toluene. The residue was then dissolved in dry acetonitrile (50 ml) and treated with N,O-dimethylhydroxylamine hydrochloride (0.73 g, 0.0075 mole) and triethylamine (4.5 ml, 0.032 mole). The mixture was stirred overnight at room temperature and then filtered to remove most of the triethylamine hydrochloride. The filtrate was evaporated to dryness and saturated potassium carbonate solution was added. The product was then extracted into chloroform (3×100 ml) and the combined extracts were dried (Na2SO4), filtered and evaporated to dryness to give the title compound (D21) as a white solid (0.79 g, 41%).

1. temperatureunder reflux for 1.5 h
2. concentrationThe reaction was then concentrated in vacuo
3. customto give a solid which
4. temperatureheated
5. temperatureunder reflux for 1.5 h
6. customThe mixture was then evaporated to dryness
7. dissolutionThe residue was then dissolved in dry acetonitrile (50 ml)
8. filtrationfiltered
9. customto remove most of the triethylamine hydrochloride
10. customThe filtrate was evaporated to dryness and saturated potassium carbonate solution
11. additionwas added
12. extractionThe product was then extracted into chloroform (3×100 ml)
13. dry with materialthe combined extracts were dried (Na2SO4)
14. filtrationfiltered
15. customevaporated to dryness

ORD record

ord-7d745817943a4707af3a6bdedbc02316

Source dataset

uspto-grants-1992_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05110828