Potassium Carbonate → 4-(4-Methylbenzyl)-4-hydroxy-1-(but-3-yn-1-yl)piperidine

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Reaction Steps

A mixture of 4-methyl-4-hydroxybenzylpiperidine hydrocholoride (1.3 g, 5.4 mmol), 1-butyn-4-yl methanesulfonate (0.96 g, 6.5 mmol), potassium carbonate (2.5 g, 18 mmol) in 50 mL of acetonitrile was allowed to reflux for 12 hrs. The inorganic salt was removed through a short column of silica gel and washed with ethyl acetate (3×30 mL). Evaporation of solvents gave a residue, which was purified by flash chromatography (50% EtOAc in hexane), giving 0.90 g (65%) of the title compound as a pale yellow oil. 1H NMR (CDCl3) 1.258 (m, 2 H), 1.883 (m, 2 H), 1.962 (m, 3 H), 2.040 (m, 2 H), 2.342 (s, 3 H), 2.399 (m, 2 H), 2.611 (m, 3 H), 2.708 (m, 2 H), 7.060-7.135 (m, 4 H).

Provenance & Evidence