Piperidine → 1-(piperidin-1-yl)butane-1,3-dione

Participants

Reaction Steps

To a solution of piperidine (4.94 ml, 50 mmol) in dry tetrahydrofuran (100 ml) at room temperature was added 4-methyleneoxetan-2-one (3.8 ml, 50 mmol) dropwise. The reaction mixture was stirred for 24 hours at room temperature, then the solvent removed under reduced pressure and the residue dissolved in ethyl acetate. The organic phase was poured into a separatory funnel and washed with 1M aqueous hydrochloric acid, water, saturated aqueous sodium bicarbonate and brine. The organic phase was separated and the solvent removed under reduced pressure to provide 1-(piperidin-1-yl)butane-1,3-dione (8.5 g, 100%) as a viscous oil. 1H NMR (CDCl3, 400 MHz) δ 3.56 (2H, app t); 3.54 (s, 2H); 3.24 (2H, app t); 2.28 (s, 3H); 1.70-1.5 (m, 6H). The compound was utilized in the next reaction without purification.

Provenance & Evidence