Potassium Carbonate → HCID 18621499, compound

Participants

Reaction Steps

A mixture of 1-benzoyloxy-4-bromobut-2-yne (1.26 g, 5.00 mmol), 4-benzylpiperidine (0.964 g, 5.50 mmol) and K2CO3 (1.52 g, 11.0 mmol) in 50 mL of CH3CN was refluxed under N2 for 24 hr. The inorganic salt was removed through a short column of silica gel and was washed with EtOAc (3×30 mL). The filtrate was evaporated in vacuo to give a residue, which was purified by flash chromatography to give the product as a brown oil (0.55 g, 32%): 1H NMR (CDCl3) d 1.34 (m, 2 H), 1.50 (m, 1 H), 1.63 (m, 2 H), 2.11 (m, 2 H), 2.51 (d, J=6.9 Hz, 2 H), 2.78 (m, 2 H), 2.86 (d, J=11.1 Hz, 2 H), 3.31 (s, 2 H), 4.94 (s, 2 H), 7.12-7.52 (m, 8 H); MS (m/z) 348 (M++1, 20), 347 (M+, 100), 346 (M+−1, 60), 226 (30), 105 (100).

Provenance & Evidence