Morpholine → HCID 70496684, compound

Participants

Reaction Steps

A mixture solution of 2-(3-bromo-phenyl)-6-chloro-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid methyl ester (8.9 g, 7 mmol), morpholine (6.1 mL, 70 mmol), copper(I) iodide (0.4 g, 2.1 mmol), N,N-dimethylglycine hydrochloride (0.4 g, 2.8 mmol), and potassium carbonate (2.9 g, 21 mmol) in dimethyl sulfoxide (20 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 6-chloro-4,4-dimethyl-2-(3-morpholin-4-yl-phenyl)-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid (2.7 g, 96%) as a white solid: MS (ESI) M+1=401.2.

Provenance & Evidence