CC1(O)C=C[C:5]([CH2:6][N:7]2[CH2:12][CH2:11]C[CH2:9][CH2:8]2)=[CH:4][CH2:3]1.CS(O[CH2:21][CH2:22][C:23]#[CH:24])(=O)=O.[C:25](=[O:28])([O-])[O-].[K+].[K+]>C(#N)C>[CH3:21][C:22]1[CH:3]=[CH:4][C:5]([CH2:6][C:25]2([OH:28])[CH2:9][CH2:8][N:7]([CH2:6][CH2:5][C:4]#[CH:3])[CH2:12][CH2:11]2)=[CH:24][CH:23]=1A 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).
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