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

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Reaction Steps

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%).

Provenance & Evidence