Nicotinic Acid → N-nicotinoyl dopamine

HRID 1633217Notes

Reaction equation

HRID 1633217 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 dopamine

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°, there was added 10.3 g (0.05 mol) dicyclohexylcarbodiimide (DCC). The reaction mixture was stirred at room temperature for 24 hrs and the formed dicyclohexylurea was removed by filtration. The pyridine was removed by distillation in vacuo and the residue was crystallized in water at 0°. 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. 156°-162°; aqueous solution of the compound gave green color with Fe-3 and reduced AgNO3TS, ir (KBr) 3300, 2960, 1725, 1630, 1590, 1520, 1430, 1290, 1190, 1115, 740 and 710 cm-1 ; pmr (d6 -DMSO) δ9.25-6.25 (m, 7H), 3.3 (m, 2H) and 2.65 (m, 2H) ppm. Anal. (C14H14N2O3) C, H, N.

Workup

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

Sources & evidence

ORD record
ord-65c91ae28ebd405da783e7b681f5a0e0
Source dataset
uspto-grants-1984_10
Patent number
US04479932

Reaction notes

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