Methylamine → Dimethyl 2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate

Participants

Reaction Steps

To a stirred solution of methylamine (40 wt % in water, 125 mL, 1.45 mol) at ambient temperature was added 4-(2-chloro-phenyl)-2-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethoxymethyl]-6-methyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid dimethyl ester (dimethylamlodipine phthalimide) (4, 6.30 g, 12.0 mmol). The reaction mixture was stirred at ambient temperature for 18 hours, then diluted with water (100 mL) and extracted with ethyl acetate (3×100 mL). The combined organic extracts were washed with saturated brine (100 mL), dried over MgSO4 and concentrated under reduced pressure to give 5 a yellow oil (4.0 g, 84% yield, 90% pure by LCMS and 1H NMR), 1H NMR (400 MHz; CDCl3): δ 7.15 (m, 1H); 7.02–7.00 (m, 3H); 4.43 (m, 1H); 4.04 (s, 2H); 3.76 (singlets, 6H total); 3.63 (m, 2H); 2.82 (m, 2H); 1.71 (s, 3H).

Provenance & Evidence