Nicotinic Acid → N-Nicotinoyl tyramine

HRID 260189Notes

Reaction equation

HRID 260189 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.Cl.[NH2:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.C1(N=C=NC2CCCCC2)CCCCC1.[2H]C(S(C([2H])([2H])[2H])=O)([2H])[2H].[2H]O[2H]>N1C=CC=CC=1>[C:1]([NH:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)(=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1

Participants

6

Reactant 4

HCID 938Nicotinic AcidHCID 10868DicyclohexylcarbodiimideHCID 66449Tyramine hydrochlorideHCID 86701925DMSO-d6 D2O

Product 1

HCID 3043417N-Nicotinoyl tyramine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent4×

Procedure

To an ice cold suspension of 3.69 g (0.03 mol) nicotinic acid in a solution of 5.2 g (0.03 mol) tyramine hydrochloride in 100 ml of pyridine, 6.18 g (0.03 mol) of dicyclohexylcarbodiimide (DCC) were gradually added while stirring. Stirring was continued 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 triturated with cold water, filtered and crystallized from 50% aqueous methanol. Yield, 6.25 g (86%), m.p. 179°-181° C. PMR (DMSO-d6 /D2O) δ 9.0-8.66 (m, 2H, C2 and C6 pyridine protons), 8.33-8.10 (m, 1H, C4 pyridine proton), 7.66-7.46 (m, 1H, C5 pyridine proton), 7.23-6.70 (m, rH, C6H4), 3.56 (t, 2H, ##STR1451## 2.90 (t, 2H, CH2). Anal. (C14H14N2O2) C, H, N.

Workup

  1. additionwere gradually added
  2. stirringStirring
  3. customthe formed dicyclohexylurea was removed by filtration
  4. customThe pyridine was removed by distillation in vacuo
  5. customthe residue was triturated with cold water
  6. filtrationfiltered
  7. customcrystallized from 50% aqueous methanol
  8. customYield

Sources & evidence

ORD record
ord-bdeed2e0ab214b4fa560e09237079bc6
Source dataset
uspto-grants-1996_06
Patent number
US05525727

Reaction notes

Loading…