Piperazine → Quinoline, 1,2,3,4-tetrahydro-4,4-dimethyl-6-(4-morpholinylsulfonyl)-2-[3-(1-piperazinyl)phenyl]-

Participants

Reaction Conditions

Reaction Steps

The mixture solution of 2-(3-bromo-phenyl)-4,4-dimethyl-6-(morpholine-4-sulfonyl)-1,2,3,4-tetrahydro-quinoline (150.0 mg, 0.33 mmol), copper(I) iodide (20.0 mg, 0.1 mmol), piperazine (283.4 mg, 3.3 mmol), N,N-dimethylglycine hydrochloride (34.0 mg, 0.24 mmol) and potassium carbonate (110.0 mg, 1.0 mmol) in dimethyl sulfoxide (2.0 mL). was stirred at 120° C. for 16 h. Then the reaction mixture was cooled to room temperature and extracted with ethyl acetate (70 mL×2), washed with water (30 mL×3) and saturated aqueous ammonium chloride solution (30 mL×2), 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 4,4-dimethyl-6-(morpholine-4-sulfonyl)-2-(3-piperazin-1-yl-phenyl)-1,2,3,4-tetrahydro-quinoline (51.1 mg, 33.0%) as a white solid: MS (ESI) M+1=471.2.

Provenance & Evidence