Morpholine → HCID 59054066, compound

Participants

Reaction Steps

The mixture solution of 2-(3-bromo-phenyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-sulfonic acid isopropylamide (392.0 mg, 0.9 mmol), CuI (51.0 mg, 0.27 mmol), N,N-dimethylglycine hydrochloride (75.0 mg, 0.54 mmol), potassium carbonate (373.0 mg, 2.7 mmol) and morpholine (0.78 mL, 9.0 mmol) in DMSO (5.0 mL) was stirred at 120° C. for 16 h under a nitrogen atmosphere. 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-2-(3-morpholin-4-yl-phenyl)-1,2,3,4-tetrahydro-quinoline-6-sulfonic acid isopropylamide (160.0 mg, 40%) as a light yellow solid: MS (ESI) M+1=444.3.

Provenance & Evidence