Methyl iodide → 1-Methyl-3-{N-[beta-(4-hydroxyphenyl)ethyl]}carbamoylpyridinium iodide

HRID 2081990Notes

Reaction equation

HRID 2081990 reaction equation
[C:1]([NH:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[CH3:19][I:20]>CC(C)=O>[I-:20].[CH3:19][N+:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:1](=[O:8])[NH:9][CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([OH:18])=[CH:16][CH:17]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 3043417N-Nicotinoyl tyramine

Product 1

HCID 134734281-Methyl-3-{N-[beta-(4-hydroxyphenyl)ethyl]}carbamoylpyridinium iodide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 1.21 g (5 mmol) of nicotinoyltyramine in 10 ml of acetone, 1.41 g (10 mmol) of methyl iodide were added and the mixture was refluxed while stirring for 6 hrs. The fine, yellow solid which separated was filtered and crystallized from methanol ether. Yield 1.78 g (93%), m.p. 208°-210° C. PMR (DMSO-d6 /D2O) δ 9.23-8.26 (m, 4H, C5H4N+), 7.33-6.83 (m, 4H, C6H4), 4.50 (s, 3H, ##STR1548## 3.70 (t, J=7 Hz, 2H, ##STR1549## 2.93 (t, J=7 Hz, 2H, CH2).

Workup

  1. temperaturethe mixture was refluxed
  2. customThe fine, yellow solid which separated
  3. filtrationwas filtered
  4. customcrystallized from methanol ether

Sources & evidence

ORD record
ord-7b9d3f98e8b648489f1a8adf548e59a7
Source dataset
uspto-grants-1993_02
Patent number
US05187158

Reaction notes

Loading…