Triethylamine → HCID 19610946, compound

Participants

Reaction Steps

3-Quinuclidinyl-hydrazine dihydrochloride (D5) (0.78 g, 3.6 mmol) was suspended in dry methanol (30 ml) and methyl acetimidate hydrochloride (0.40 g, 3.65 mmol) added, followed by triethylamine (1.52 ml, 3 eq). The solution was stirred for 3 h at room temperature under N2, and then evaporated to dryness under reduced pressure at a temperature not exceeding 30° C. Anhydrous triethylorthoformate (40 ml) and anhydrous pyridine (4 ml) were added, and the suspension was stirred overnight at room temperature under N2 and then refluxed under N2 for 1.5 h. The mixture was cooled, evaporated to dryness under reduced pressure and the residue was dissolved in saturated aqueous potassium carbonate solution (40 ml). The solution was extracted with ethyl acetate (2×300 ml), the organic extracts dried (Na2SO4), filtered and evaporated to dryness under reduced pressure. The resulting oil was purified by column chromatography using neutral alumina and with gradient elution using ethyl acetate to 2% methanol in ethyl acetate. The resulting clear oil was crystallised as the dihydrochloride salt using diethyl ether/methanol solution and recrystallised in acetone/ether to afford the title compound as white crystals (110 mg, 13%), m.p. >250° C.

Provenance & Evidence