Morpholine → HCID 70497656, compound

Participants

Reaction Steps

A mixture solution of 2-(5-bromo-2-methyl-phenyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid methyl ester (3.5 g, 8.7 mmol), morpholine (7.6 mL, 87 mmol), copper(I) iodide (1 g, 5.22 mmol), N,N-dimethylglycine hydrochloride (0.97 g, 6.96 mmol), and potassium carbonate (3.6 g, 26.1 mmol) in dimethyl sulfoxide (25 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 (200 mL×2), washed with saturated aqueous ammonium chloride solution (50 mL×3) and brine (50 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-(2-methyl-5-morpholin-4-yl-phenyl)-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (3.2 g, 90%) as a white solid: MS (ESI) M+1=409.0.

Provenance & Evidence