Potassium Carbonate → 4-Benzyl-4-hydroxy-1-(4-(3-methylphenyl)-3-butynyl)piperidine

Participants

Reaction Steps

A mixture of 1-mesyl-4-(3-methylphenyl)but-3-yne (344 mg, 1.45 mmol), 4-benzyl-4-hydroxy-piperidine (332 mg, 1.73 mmol) and K2CO3 (598 mg, 4.34 mmol) in 15 mL of CH3CN is refluxed for 12 hr. The mixture is filtered and washed with EtOAc (3×20 ml). The filtrate is evaporated in vacuo and is purified by flash chromatography to give the product as a brown oil (100 mg, 20%): 1H NMR (CDCl3) 1.37 (s, 1 H), 1.55 (m, 2 H), 1.75 (m, 2 H), 2.30 (s, 3 H), 2.41 (m, 2 H), 2.60 (m, 3 H), 2.75 (m, 5 H), 7.11-7.31 (m, 9 H).

Provenance & Evidence