Nicotinic Acid → N-nicotinoyl dopamine

Participants

Reaction Steps

To a pyridine solution containing 11.7 g (0.05 mol) dopamine hydrobromide and 6.15 g (0.05 mol) nicotinic acid at 0°, there was added 10.3 g (0.05 mol) dicyclohexylcarbodiimide (DCC). The reaction mixture was stirred at room temperature for 24 hrs and the formed dicyclohexylurea was removed by filtration. The pyridine was removed by distillation in vacuo and the residue was crystallized in water at 0°. The product was isolated by filtration and dried over phosphorous pentoxide. Recrystallization from isopropanol gave 9.0 g (0.035 mol), 70%, N-nicotinoyldopamine, m.p. 156°-162°; aqueous solution of the compound gave green color with Fe-3 and reduced AgNO3TS, ir (KBr) 3300, 2960, 1725, 1630, 1590, 1520, 1430, 1290, 1190, 1115, 740 and 710 cm-1 ; pmr (d6 -DMSO) δ9.25-6.25 (m, 7H), 3.3 (m, 2H) and 2.65 (m, 2H) ppm. Anal. (C14H14N2O3) C, H, N.

Provenance & Evidence