Morpholine → HCID 67441534, compound

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 (5.7 g, 14.7 mmol), morpholine (12.8 mL, 147 mmol), copper(I) iodide (1.68 g, 8.8 mmol), N,N-dimethylglycine hydrochloride (1.58 g, 11.8 mmol), and potassium carbonate (6.1 g, 44.1 mmol) in dimethyl sulfoxide (30 mL) was stirred at 120° C. for 16 h. Then the reaction mixture cooled to room temperature. The reaction mixture was extracted with ethyl acetate (2×150 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-morpholin-4-yl-phenyl)-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (5.6 g, 96%) as a white solid which was used for next step without further purification: LC/MS m/e calcd for C24H30N2O3 (M+H)+: 395.52, observed: 395.2.

Provenance & Evidence