Triethylamine → HCID 19610943, compound

Participants

Reaction Steps

3-Quinuclidyl-hydrazine dihydrochloride salt (D5) (200 mg, 1.0 mmol) and Gold's reagent ([3-(dimethylamino)-2-azaprop-2-en-1-ylidene]-dimethylammonium chloride) (153 mg, 1.0 mmol) were dissolved in dry CHCl3 (20 ml) under N2 and dry Et3N (0.28 ml, 2.0 mmol) was added. The solution was heated at reflux under nitrogen for 2.5 h. The solution was cooled, saturated aqueous potassium carbonate was added and the organic layer separated. The aqueous layer was extracted with CHCl3 (2×100 ml), the organic extracts were dried (Na2SO4), filtered and were evaporated to dryness under reduced pressure. The resulting orange/yellow oil was purified by column chromatography (basic alumina eluting with 2% MeOH/EtOAc). The resulting clear oil was recrystallised as the dihydrochloride salt from methanol/acetone/diethyl ether (45 mg, 0.18 mmol, 18%), m.p. 187-190° C.

Provenance & Evidence