4-[(4-chlorophenyl)methyl]piperidine;hydrochloride

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1-mesylbut-3-yne (2.22 g, 15.0 mmol), 4-(4-chlorobenzyl)piperidine hydrochloride (2.95 g, 12.0 mmol), K2CO3 (4.97 g, 36.0 mmol) in 50 mL of CH3CN is allowed to reflux for 12 hr. The inorganic salt is removed through a short column of silica gel and washed with EtOAc (3×30 mL). Evaporation of solvents gives a residue, which is purified by flash chromatography giving the product as pale yellow oil (2.67 g, 85%): 1H NMR (CDCl3) 1.31 (m, 2 H), 1.50 (m, 1 H), 1.59 (m, 2 H), 1.96 (m, 3 H), 2.38 (m, 2 H), 2.48 (m, 2 H), 2.55 (m, 2 H), 2.88 (d, J=11.1 Hz, 2 H), 7.04 (d, J=8.1 Hz, 2 H), 7.26 (d, J=8.1 Hz, 2 H). to reflux for 12 hr The inorganic salt is removed through a short column of silica gel washed with EtOAc (3×30 mL) Evaporation of solvents gives a residue, which is purified by flash chromatography