Hydrazinecarboxaldehyde → HCID 54767655, compound

Participants

Reaction Conditions

Reaction Steps

A 100-mL round-bottomed flask was charged with a solution of methyl 1-((9-ethyl-9H-carbazol-3-yl)methyl)piperidine-3-carbimidate hydrochloride (1.44 g, 3.94 mmol, 1.00 equiv, 1.44%) in pyridine (20 mL) and formohydrazide (0.249 g, 4.07 mmol, 1.03 equiv, 0.249%). The resulting solution was stirred overnight at 110° C. in an oil bath. Upon completion, the resulting solution was cooled down to room temperature and diluted with water. This mixture was then extracted with ethyl acetate (3×30 mL). Combined organic layers were dried over anhydrous sodium sulfate. After filtration, organic later was concentrated on a rotary evaporator to give a residue that was purified by a silica gel column chromatography eluted with ethyl acetate/hexane (1:10) affording 3-((3-(2H-1,2,4-triazol-3-yl)piperidin-1-yl)methyl)-9-ethyl-9H-carbazole as white solid (0.011 g, 1%). LCMS: [M+H]+: 360. 1H NMR (CDCl3, 300 MHz) δ 11.55 (s, 1H), 8.10 (m, 3H), 7.68 (d, 1H), 7.50 (t, 1H), 7.38 (m, 2H), 7.25 (t, 1H), 4.35 (t, 3H), 3.76 (d, 2H), 3.50 (d, 1H), 2.66 (s, 1H), 2.32 (d, 1H), 2.12 (d, 1H), 2.01 (d, 1H), 1.84 (d, 1H), 1.55 (d, 1H), 1.39 (t, 3H).

Provenance & Evidence