Thionyl Chloride → 4-(2-Piperidin-1-ylethoxy)benzoyl chloride hydrochloride

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Reaction Steps

A 500 mL round-bottom flask is charged with 4-(2-piperidin-1-yl-ethoxy)-benzoic acid hydrochloride, (25 g, 0.08748 mol) and thionyl chloride (150 mL, 2.0564 mol). The mixture is brought to reflux for 15 minutes whereupon it becomes a clear solution. The reaction is cooled to room temperature and the excess thionyl chloride is removed to give a quantitative yield of the desired product. 1H NMR: ∂ 8.08 (app. d, J=8.8 Hz, 2H), 6.99 (app. d, J=9.2 Hz, 2H), 4.71 (t, J=4.6 Hz, 2H), 3.65 (d, J=12 Hz, 2H), 3.43 (quart., J=4.6 Hz, 2H), 2.76–2.85 (m, 2H), 2.22–2.32 (m, 2H), 1.87–1.94 (m, 3H), 1.37–1.49 (m, 1H).

Provenance & Evidence