4-(Piperidin-1-yl)aniline → HCID 22124623, compound

Participants

Reaction Steps

A stirred solution of (XV, where R2 is ethyl) (100 mg, 0.52 mmol), 4-(1-piperidinyl)aniline (0.26 g, 1.12 mmol) in THF (5.0 mL) under nitrogen at -78° C. was treated with a solution (0.8 mL, 1.2 mmol) of lithium diisopropylamide (1.5 M in cyclohexane), then the temperature was allowed to rise slowly to 20° C. overnight. The resulting solution was treated with 3 drops of glacial acetic acid and concentrated to a dark residue that was purified that purified by silica gel chromatography eluting with EtOAc. The product fractions were pooled and concentrated to a foam that was crystallized to give ethyl-7-(4-(piperidin-1-yl)phenylamino)-1H -[1,6]naphthyridin-2-one (79 mg, 44%): mp (CH2Cl2 /hexanes) 137-139° C.

Provenance & Evidence