Isopropylamine → 2-(3-Isopropylamino-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester

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 (970 mg, 2.5 mmol), isopropylamine (1 mL, 12.5 mmol), copper(I) iodide (285 mg, 1.5 mmol), N,N-dimethylglycine hydrochloride (280 g, 2 mmol), and potassium carbonate (3.455 g, 25 mmol) in dimethyl sulfoxide (15 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 2-(3-isopropylamino-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (915 mg, 90%) as a light yellow solid which was used for next step without further purification: LC/MS m/e calcd for C23H30N2O2 (M+H)+: 367.51, observed: 367.2.

Provenance & Evidence