Nicotinic Acid → N-nicotinoyl dopamine

HRID 1719475Notes

Reaction equation

HRID 1719475 reaction equation
Br.[NH2:2][CH2:3][CH2:4][C:5]1[CH:12]=[CH:11][C:9]([OH:10])=[C:7]([OH:8])[CH:6]=1.[C:13](O)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[N:16][CH:15]=1.C1(N=C=NC2CCCCC2)CCCCC1>N1C=CC=CC=1>[C:13]([NH:2][CH2:3][CH2:4][C:5]1[CH:12]=[CH:11][C:9]([OH:10])=[C:7]([OH:8])[CH:6]=1)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[N:16][CH:15]=1

Participants

5

Reactant 3

HCID 938Nicotinic AcidHCID 10868DicyclohexylcarbodiimideHCID 715644-(2-Aminoethyl)pyrocatechol hydrobromide

Product 1

HCID 13473418N-nicotinoyl dopamineYield 70%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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. (C14H14N2O 3) C, H, N.

Workup

  1. customthe formed dicyclohexylurea was removed by filtration
  2. customThe pyridine was removed in vacuo
  3. customthe residue was crystallized from water at 0° C
  4. customThe product was isolated by filtration
  5. dry with materialdried over phosphorous pentoxide
  6. customRecrystallization from isopropanol

Sources & evidence

ORD record
ord-b12099a7bcdc4d708decc9207b16949d
Source dataset
uspto-grants-1985_09
Patent number
US04540564

Reaction notes

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