HCID 67057621, compound → HCID 67057593, compound

Participants

Reaction Steps

To a stirred solution of methyl 4-(2-(benzhydryloxy)ethyl)-5,6-dihydropyridine-1(2H)-carboxylate (6.5 g, 18.49 mmol) in ethanol (25 ml) was added Claisen's alkali (6.457 g KOH dissolved in 5 ml water and 20 ml methanol). The solution was refluxed overnight, concentrated in vacuo, cooled and diluted with water (40 ml) and extracted with ether (3×30 ml). The combined ethereal extract was dried (Na2SO4) and evaporated to afford viscous liquid. The product was purified by column chromatography over silica gel (ethyl acetate:methanol:triethylamine 20:10:2.5) to obtain compound 5 as yellowish viscous liquid (4.8 g, 88%). 1H-NMR (CDCl3; 400 MHz): 2.03 (brm, 2H, H-3), 2.29-2.32 (t, 2H, J=6.4 Hz, OCH2CH2), 2.92-2.95 (t, 2H, J=5.6 Hz, H-2), 3.31 (brs, 2H, H-6), 3.49-3.53 (t, 2H, OCH2CH2), 5.32 (s, 1H, PhCH(O)Ph), 5.41 (brs, 1H, CH═C), 5.76 (brs, 1H, —NH), 7.17-7.33 (m, 10H, ArH).

Provenance & Evidence