Piperidine → (1E,6E)-1-(1H-indol-6-yl)-7-[2-methoxy-4-[(4-methylpiperazin-1-yl)methyl]phenyl]hepta-1,6-diene-3,5-dione

Participants

Reaction Conditions

Reaction Steps

To 200 mL of a solution of 7.56 g of (E)-6-(1H-indol-6-yl)hex-5-ene-2,4-dione in AcOEt was added 3.24 g of boron oxide, and the mixture was stirred at 70° C. for 1 hour. To this, 15 mL of a solution of 8.68 g of 2-methoxy-4-[(4-methylpiperazin-1-yl)methyl]benzaldehyde in AcOEt and 18.3 mL of triisopropyl borate were successively added, and the mixture was stirred at the same temperature for 40 minutes. Then, 10 mL of a solution of 0.35 mL of piperidine in AcOEt was added. The mixture was stirred at 70° C. for 3 hours and was allowed to cool back to room temperature. To the reaction mixture, 100 mL of a 10% K2CO3 aqueous solution was added, and the mixture was stirred for 1 hour. The organic layer was separated and concentrated. The residue was purified by amino-silica gel column chromatography (heptane/AcOEt system) to give 7.14 g of the title compound (47% yield).

Provenance & Evidence