Morpholine → HCID 70497766, compound

Participants

Reaction Steps

A mixture solution of 2-(3-bromo-phenyl)-4,4,8-trimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid methyl ester (1.4 g, 3.6 mmol), morpholine (4.3 mL, 50 mmol), copper(I) iodide (274 mg, 1.44 mmol), N,N-dimethylglycine hydrochloride (0.3 g, 2.16 mmol), and potassium carbonate (1.49 g, 10.8 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 (150 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 4,4,8-trimethyl-2-(3-morpholin-4-yl-phenyl)-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid methyl ester (1.4 g, 98%) as a white solid: MS (ESI) M+1=394.2.

Provenance & Evidence