Potassium Carbonate → HCID 57244914, compound

Participants

Reaction Steps

A solution of [2S,3S]-2-phenyl-3-[(5-(1-methyl-1H-[1,2,3]triazol-5-yl)benzofuran-7-yl)methyloxy]piperidine hydrochloride (230 mg) in N,N-dimethylformamiide (2 ml) was slowly added to a solution of 1,4-dichlorobut-2-yne (106 ml) and potassium carbonate (224 mg) in N,N-dimethylformamide (2.0 ml). The solution was stirred for 18 hours at room temperature and the solvent removed under reduced pressure. To the residue was added water (40 ml) and the product was extracted with ethyl acetate (3×10 ml). The combined organic fractions were washed with water, saturated brine, dried over MgSO4, filtered and the solvent removed under reduced pressure. The residue was purified by MPLC (10% ethyl acetate/hexane) to give [2S,3S]-1-(4-chlorobut-2-yn-1-yl)-2-phenyl-3-[(5-(1-methyl-1H-[1,2,3]triazol-5-yl)benzofuran-7-yl)methyloxy]piperidine as a yellow oil (205 mg). 1H NMR (360 MHz,CDCl3) δ1.57 (2H, m), 2.22 (2H, m), 2.98 (1H, m), 3.27 (2H, d, J=3.0 Hz), 3.43 (1H, br s), 3.62 (1H, br s), 3.95 (3H, s), 4.13 (2H, s), 4.46 (1H, d, J=11.0 Hz), 4.82 (2H, d, J=11.0 Hz), 6.77 (1H, d, J=1.0 Hz), 6.87 (1H, s), 7.15 (3H, m), 7.38 (2H, m), 7.43 (1H, s), 7.62 (2H, br s); MS m/z (CI+) 475 (M+H+).

Provenance & Evidence