Ethylamine → HCID 46870291, compound

Participants

Reaction Steps

3-Allyl-2-(methylsulfonyl)-3H-spiro[benzo[h]quinazoline-5,1′-cyclohexan]-4(6H)-one (6, 306 mg, 0.796 mmol) and potassium carbonate (165 mg, 1.19 mmol) were added to 1 mL of dry dimethylformamide stirring under nitrogen atmosphere. A 2.0M solution of ethylamine in tetrahydrofuran (1 mL, 2 mmol) was then added, and the reaction was tightly capped and allowed to stir at room temperature for 5 hours. Another 1 mL portion of ethylamine solution was added at 5 hours, and the reaction allowed to stir for another 12 hours. At this point, the reaction mixture was diluted with diethyl ether and washed twice with water and once with brine. The organic layer was dried over MgSO4, vacuum filtered, and concentrated in vacuo. The residue was then loaded onto a silica flash column (50 g column, 10% to 33% ethyl acetate:hexanes), which isolated title compound in 85% yield (237 mg, 0.678 mmol) as a white crystalline solid. 1H NMR (500 MHz, CDCl3) δ ppm: 8.15, 7.33, 7.22, 5.94, 5.35, 5.31, 3.60, 3.04, 2.61, 1.72, 1.58, 1.39, 1.30.

Provenance & Evidence