Potassium Carbonate → 3,3-Dimethyl-2-[3-(4-o-tolyl-piperazin-1-yl)-phenyl]-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(3-bromo-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (1.2 g, 3.1 mmol), 1-o-tolyl-piperazine (987 mg, 4.6 mmol), copper(I) iodide (180 mg, 0.93 mmol), N,N-dimethylglycine hydrochloride (260 mg, 1.86 mmol) and potassium carbonate (1.3 g, 9.3 mmol) in dimethyl sulfoxide (10 mL) was stirred at 120° C. for 16 hours. Then the reaction mixture cooled to room temperature. The reaction mixture was extracted with ethyl acetate (2×200 mL), washed with water (2×50 mL) and saturated aqueous ammonium chloride solution (2×50 mL), dried over anhydrous sodium sulfate and then concentrated in vacuo to afford 3,3-dimethyl-2-[3-(4-o-tolyl-piperazin-1-yl)-phenyl]-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (1.2 g, 80%) as a light yellow oil which was used for next step without further purification: LC/MS m/e calcd for C31H37N3O2 (M+H)+: 484.56, observed: 484.2.

Provenance & Evidence