Nicotinic Acid → N-Nicotinoyl tyramine

HRID 621674Notes

Reaction equation

HRID 621674 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, ##STR1535## 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-000018d6f8904d8db6ec46fe95ee94a2
Source dataset
uspto-grants-1989_04
Patent number
US04824850

Reaction notes

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