N,N'-Dimethylethylenediamine → 3,3-Dimethyl-2-{3-[methyl-(2-methylamino-ethyl)-amino]-phenyl}-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid

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Reaction Conditions

Reaction Steps

A mixture of 2-(3-bromo-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (600 mg, 1.7 mmol), N,N′-dimethyl-ethane-1,2-diamine (0.37 mL, 3.4 mmol), copper(I) iodide (96 mg, 0.5 mmol), N,N-dimethylglycine hydrochloride (140 mg, 1.0 mmol) and potassium carbonate (923 mg, 6.7 mmol) in dimethyl sulfoxide (5 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. Purification by Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) afforded 3,3-dimethyl-2-{3-[methyl-(2-methylamino-ethyl)-amino]-phenyl}-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (500 mg, 80%) as a white solid: LC/MS m/e calcd for C22H29N3O2 (M+H)+: 368.50, observed: 368.1.

Provenance & Evidence