Reaction #4668

Reaction equation

dopamine hydrobromide

nicotinic acid

dicyclohexylcarbodiimide

→

N-nicotinoyldopamine

Yield 70.0%

Solvents

pyridine

Conditions

Workup

1. 1
   Otherthe formed dicyclohexylurea was removed by filtration
2. 2
   OtherThe pyridine was removed in vacuo
3. 3
   Otherthe residue was crystallized from water at 0° C
4. 4
   OtherThe product was isolated by filtration
5. 5
   Dryingdried over phosphorous pentoxide
6. 6
   OtherRecrystallization from isopropanol

Procedure

To a pyridine solution containing 11.7 g (0.05 mol) dopamine hydrobromide and 6.15 g (0.05 mol) nicotinic acid at 0° C. were added 10.3 g (0.05 mol) dicyclohexylcarbodiimide (DCC). The reaction mixture was stirred at room temperature for 24 hours and the formed dicyclohexylurea was removed by filtration. The pyridine was removed in vacuo and the residue was crystallized from water at 0° C. 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. 159°-162° C.; aqueous solution of the compound gave a green color with Fe+3 and reduced AgNO3 ; ir (KBr) 3300, 2960, 1725, 1630, 1590, 1520, 1430, 1290, 1190, 1115, 720 and 710 cm-1 ; NMR (d6 -DMSO) δ 9.25-6.25 (m, 7H), 3.3 (m, 2H) and 2.65 (m, 2H) ppm. Anal. (C14H14N2O3) C, H, N.

Source