반응 #4668

반응 방정식

dopamine hydrobromide

nicotinic acid

dicyclohexylcarbodiimide

→

N-nicotinoyldopamine

수율 70.0%

용매

pyridine

반응 조건

후처리

1. 1
   기타the formed dicyclohexylurea was removed by filtration
2. 2
   기타The pyridine was removed in vacuo
3. 3
   기타the residue was crystallized from water at 0° C
4. 4
   기타The product was isolated by filtration
5. 5
   건조dried over phosphorous pentoxide
6. 6
   기타Recrystallization from isopropanol

실험 절차

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.

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