Sodium Bicarbonate → 1-Piperazin-1-yl-1,9a-dihydro-quinolizin-4-one

Participants

Reaction Steps

A mixture of 1-(4-tert-Butoxycarbonyl-piperazin-1-yl)-4-oxo-1,9a-dihydro-4H-quinolizine-3-carboxylic acid ethyl ester (0.320 g, 0.797 mmol) in concentrated HCl (5 mL) was refluxed for 30 minutes. After cooling, the reaction was basified with aqueous NaHCO3 solution and thoroughly extracted with DCM. The combined organic layers were washed with brine, dried and concentrated to give 1-Piperazin-1-yl-1,9a-dihydro-quinolizin-4-one (0.075 g, 41%) as a yellow oil. 1H NMR (CDCl3, 400 MHz) δ 9.16 (d, J=7.2 Hz, 1H), 8.20 (d, J=9.2 Hz, 1H), 7.71 (d, J=9.6 Hz, 1H), 7.37 (t, J=7.2 Hz, 1H), 7.03 (t, J=6.4 Hz, 1H), 6.61 (d, J=9.2 Hz, 1H), 3.07 (m, 4H), 2.87 (m, 4H). LCMS (APCI+) m/z 230 [M+H]+; Rt=0.29 min.

Provenance & Evidence