Morpholine → HCID 70496383, compound

Participants

Reaction Steps

A mixture solution of 2-(5-bromo-2-chloro-phenyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid methyl ester (3 g, 7 mmol), morpholine (6.2 mL, 71 mmol), copper(I) iodide (0.8 g, 4.2 mmol), N,N-dimethylglycine hydrochloride (0.78 g, 5.6 mmol), and potassium carbonate (2.9 g, 21 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 2-(2-chloro-5-morpholin-4-yl-phenyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (2.8 g, 93%) as a white solid: MS (ESI) M+1=429.1.

Provenance & Evidence