反应 #4668

反应方程式

dopamine hydrobromide

nicotinic acid

dicyclohexylcarbodiimide

→

N-nicotinoyldopamine

收率 70.0%

溶剂

pyridine

反应条件

后处理

1. 1
   其他the formed dicyclohexylurea was removed by filtration
2. 2
   其他The pyridine was removed in vacuo
3. 3
   其他the residue was crystallized from water at 0° C
4. 4
   其他The product was isolated by filtration
5. 5
   干燥dried over phosphorous pentoxide
6. 6
   其他Recrystallization from isopropanol

实验过程

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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