Potassium Carbonate → HCID 70497846, compound

Participants

Reaction Steps

A mixture solution of 2-(3-bromo-phenyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid methyl ester (1.94 g, 5 mmol), 1-methyl-piperazine (2.2 mL, 20 mmol), copper(I) iodide (0.38 g, 2 mmol), N,N-dimethylglycine hydrochloride (0.42 g, 3 mmol), and potassium carbonate (2.07 g, 15 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-6-carboxylic acid methyl ester (0.61 g, 30%) as a yellow solid: MS (ESI) M+1=407.1.

Provenance & Evidence