Ethyl Acetate → HCID 18686769, compound

Participants

Reaction Steps

To a solution of (3-chloro-6-nitro-2-piperidin-1-ylmethyl-phenyl)-(4-methoxy-benzyl)-amine (22) (0.389 g, 1 mmol) in CH2Cl2 (5 mL) and H2O (0.25 mL), DDQ was added at room temperature under vigorous stirring. The dark reaction mixture was monitored by TLC (SiO2, Hexanes:EtOAc, 8:2) and additional DDQ (0.345 g, 1 mmol) was added. The reaction mixture was filtered after additional 2 hours of stirring and diluted with saturated aqueous NaHCO3 solution (100 mL). The product was extracted with CH2Cl2 (2×100 mL), and the extracts were washed with saturated NaCl solution (2×200 mL) and dried (MgSO4). Dark oil (1.68 g) was chromatographed (SiO2, Hexanes:EtOAc, 9:1 to 8:2) twice to give the desired aniline derivative as a yellow solid. Yield: 0.68 g, 25%. 1H-NMR (CDCl3) δ 1.43 (m, 2H), 1.53 (m, 4H), 2.38 (m, 4H), 3.75 (s, 2H), 6.6 (d, 1H, J=9.2 Hz), 7.95 (d, 1H, J=9.2 Hz). MS (CI) m/z 270 (M+H), 272 (M+2H). Anal Calcd for C12H16N3O2Cl: C, 53.44; H, 5.98; N, 15.58. Found: C, 53.76; H, 5.91; N, 15.01.

Provenance & Evidence