1-Benzylpiperazine → 8-(4-Benzyl-piperazin-1-yl)-6-methoxy-4-oxo-4H-chromene-2-carboxylic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

Tris(dibenzylideneacetone)dipalladium(0) (0.280 g, 0.31 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.457 g, 0.73 mmol), ethyl 8-bromo-6-methoxy-4-oxo-4H-chromene-2-carboxylate (2 g, 6.11 mmol), 1-benzylpiperazine (1.169 mL, 6.73 mmol) and cesium carbonate (2.79 g, 8.56 mmol) were heated under argon to 80 °C in toluene (60 mL) overnight. The reaction mixture was allowed to cool. Ethylacetate was added and the organic mixture was filtered. The filtrate was evaporated onto Silica gel. The crude product was added to a silica gel column and was eluted with MeOH/DCM 0-5%. 1H NMR in CDCl3 is consistent with desired product MS (m+1) = 423. HPLC Peak RT = 3.38 minutes is product. Purity = 63%.

Provenance & Evidence