Triethylamine → (4-(4-Chlorophenoxy)piperidin-1-yl)(8-hydroxyquinolin-2-yl)methanone

Participants

Reaction Conditions

Reaction Steps

To a solution of 8-hydroxyquinoline-2-carboxylic acid (15 mg, 0.079 mmol), 4-(4-chlorophenoxy)piperidine (20 mg, 0.096 mmol), and triethylamine (0.044 mL, 0.32 mmol) in DMF was added HBTU (46 mg, 0.12 mol) at room temperature. The reaction mixture was stirred at 60° C. for 2 hours. The mixture was diluted with ethyl acetate (3 mL) and washed with water (1.5 mL). The organic layer was dried over sodium sulfate, and concentrated by N2-flow. The residue was diluted with methanol and applied onto a strong cation exchange cartridge (BondElute(registered trademark) SCX, 1 g/6 mL, Varian Inc.), and the solid phase matrix was rinsed with methanol (6 mL). The crude mixture was eluted in a collection tube with 1 mol/L ammonia in methanol (6 mL) and concentrated by N2-flow. The residue was purified by preparative LC-MS to give 6.6 mg (22% yield) of the title compound.

Provenance & Evidence