Methyl vinyl ketone → 4-(4-Chlorobenzyl)-1-(3-hydroxybutyl)piperidine hydrochloride

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To a solution of 4-(4-chlorobenzyl)piperidine (1.0 g, 4.78 mmol) in methyl vinyl ketone (1.0 ml) was added H2O (1 drop) and the resulting solution stirred at 110° C. for 2 h. The crude mixture was purified by filtration on silica gel using CH2Cl2/MeOH as eluant to afford the title compound (1.20 g, 90%) as a pale yellow oil: 1H NMR (CDCl3) 1.35-1.55 (m, 5H), 1.63 (d, J =12.3, 2H), 2.055 (t, J=9.6, 2H), 2.154 (s, 2H), 2.40 (d, J=6.3, 2H), 2.748 (s, 2H), 2.972 (d, J=11.4, 2H), 7.034 (d, J=8.1, 2H), 7.218 (d, J=8.1, 2H).

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