تفاعل #4668

معادلة التفاعل

dopamine hydrobromide

nicotinic acid

dicyclohexylcarbodiimide

→

N-nicotinoyldopamine

المردود 70.0%

المذيبات

pyridine

ظروف التفاعل

المعالجة

1. 1
   أخرىthe formed dicyclohexylurea was removed by filtration
2. 2
   أخرىThe pyridine was removed in vacuo
3. 3
   أخرىthe residue was crystallized from water at 0° C
4. 4
   أخرىThe product was isolated by filtration
5. 5
   تجفيفdried over phosphorous pentoxide
6. 6
   أخرىRecrystallization from isopropanol

الإجراء التجريبي

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.

المصدر