Potassium Carbonate → HCID 70498580, compound

Participants

Reaction Steps

A mixture solution of 2-(3-bromo-phenyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid methyl ester (1.5 g, 4 mmol), 1-methyl-piperazine (1.8 mL, 16 mmol), copper(I) iodide (0.46 g, 2.4 mmol), N,N-dimethylglycine hydrochloride (0.45 g, 3.2 mmol), and potassium carbonate (1.66 g, 12 mmol) in dimethyl sulfoxide (10 mL) was stirred at 120° C. for 16 h. Then the reaction mixture was cooled to room temperature. The reaction mixture was extracted with ethyl acetate (50 mL×2), washed with saturated aqueous ammonium chloride solution (20 mL×3) and brine (20 mL×2), dried over anhydrous sodium sulfate and then concentrated in vacuo and the residue was purified by ISCO combi-flash chromatography (gradient elution, 30-50% ethyl acetate in petroleum ether) to afford 4,4-dimethyl-2-[3-(4-methyl-piperazin-1-yl)-phenyl]-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid methyl ester (0.2 g, 13%) as a white solid: MS (ESI) M+1=394.2.

Provenance & Evidence