Triethylamine → Ethyl 3-oxo-3-[4-(4-oxo-1-piperidineyl)anilino]propanoate

Participants

Reaction Steps

To a stirred solution, under N2 atmosphere, of 1-(4-amino-phenyl)-piperidine-4-one hydrochloride (which was obtained in Example 224) (10.0 g, 38 mmol), and triethylamine (15.35 g, 150 mmol) in methylene chloride (100 mL) was added ethyl 3-chloro-3-oxopropionate (6.32 g, 42 mmol). The reaction was stirred for 18 hours. The reaction mixture was concentrated down in vaco and purified by flash silica gel chromatography eluting with 1:1 ethyl acetate / hexanes to give an orange solid (0.86 g, 7%); 1H NMR (300 MHz, CDCl3) δ 1.32 (t, J=7.2 Hz, 3H), 2.55 (t, J=6 Hz, 4H), 3.46 (s, 2H), 3.56 (t, J=6 Hz, 4H), 4.22 (q, J=7.2 Hz, 2H), 6.93 (d, J=9.0 Hz, 2H), 7.47 (d, J=9.0 Hz, 2H), 9.09 (s, 1H); MS (ES) m/z: 305.3 (MH+, 100%).

Provenance & Evidence