Triethylamine → Quinoline-6-carboxylic acid 4-benzylamino-benzylamide

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Reaction Steps

The resulting (4-aminomethyl-phenyl)-benzylamine (162 mg, 0.763 mmol), quinoline-6-carboxylic acid (132 mg, 0.736 mmol), benzotriazol-1-yl-tris(dimethylamino)phosphonium hexafluorophosphate (506 mg, 1.14 mmol) and triethylamine (319 μl, 2.29 mmol) were dissolved in N,N-dimethylformamide (4.0 mL), and the solution was stirred for 2 hours at room temperature. Water was added to the reaction solution, which was then extracted with ethyl acetate, the organic layer was washed with water and brine and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, the residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=1:1), and the title compound (224 mg, 0.610 mmol, 80%) was obtained as a white solid.

Provenance & Evidence