Ethanol → Ethyl 6-oxopiperidine-3-carboxylate

Participants

Reaction Steps

To a suspension of 250 g of 5-carboxy-2-piperidone in 2.5 liters of punctilious ethanol were added 500 g of thionyl chloride at 22° C. Stir for 18 hours. The resulting solution was evaporated to dryness and the residue triturated with ether to give 233 g of the title compound: MS m/z 171 (M+), 142, 126, 115, 98; 300-MHz 1H NMR (DMSO-d6) δ1.21 (t, J=7 Hz, 3H), 1.78-1.92 (m, 1 H), 1.95-2.08 (m, 1H), 2.15-2.31 (m, 2H), 2.78-2.89 (m, 1H), 3.25-3.40 (m, 2H), 4.12 (t, J=7 Hz, 2H), 7.95 (s, 1H).

Provenance & Evidence