Thionyl Chloride → 1-Acetylpiperidine-4-carbonyl chloride

Participants

Reaction Steps

N-acetylisonipecotic acid (0.67 g, 3.9 mmol) was added to SOCl2 (4.1 mL). The acid chloride precipitated from solution and petrol (60 mL) was added. The mixture was filtered and the residue was washed several times with petrol to afford the title compound as a white solid (0.716 g, 97%). m.p. 133-138° C. 1H NMR (DMSO): 1.2-1.5 (m, 2H), 1.65-2.0 (m, 2H), 1.94 (s, 3H), 2.3-2.5 (m, 1H), 2.639 (t, J=11.4 Hz, 1H), 3.036 (t, J=11.4 Hz, 1H), 3.692 (d, J=13.2 Hz, 1H), 4.144 (d, J=13.2 Hz, 1H). IR (KBr): 1789, 1745, 1660 (cm−1). MS (m/z): 189, 126, 146, 84.

Provenance & Evidence