反応 #4668

反応方程式

dopamine hydrobromide

nicotinic acid

dicyclohexylcarbodiimide

→

N-nicotinoyldopamine

収率 70.0%

溶媒

pyridine

反応条件

後処理

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

実験手順

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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