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

HRID 260192Notes

Reaction equation

HRID 260192 reaction equation
[C:1]([O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][NH:16][C:17]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)=[O:18])=[CH:10][CH:9]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[CH3:25][I:26]>CC(C)=O>[I-:26].[CH3:25][N+:21]1[CH:22]=[CH:23][CH:24]=[C:19]([C:17](=[O:18])[NH:16][CH2:15][CH2:14][C:11]2[CH:12]=[CH:13][C:8]([O:7][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])=[CH:9][CH:10]=2)[CH:20]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 134734273-{N-[beta-(4-pivalyloxyphenyl)ethyl]}carbamoylpyridine

Product 1

HCID 134734291-Methyl-3-{N-[beta-(4-pivalyloxyphenyl)ethyl]}carbamoylpyridinium iodide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 1.63 g (5 mmol) of the product of Example 26 in 10 ml of acetone, 1.41 g (10 mmol) methyl iodide were added and the mixture was refluxed overnight while stirring. The acetone layer was separated by decantation and the yellowish, oily residue was crystallized from methanol/ether. Yield, 1.94 g (83%), m.p. 155°-157° C. PMR (D2O) δ 9.16-8.00 (m, 4H, C5H4N+), 7.33-6.83 (m, 4H, C6H4), 4.40 (s, 3H, N+ --CH3), 3.5 (t, 2H, J=7 Hz, ##STR1455## 2.90 (t, 2H, J=7 Hz, CH2), 1.30 (s, 9H, C--(CH3)3). Anal. (C20H25N2O3I) C, H, N.

Workup

  1. temperaturethe mixture was refluxed overnight
  2. customThe acetone layer was separated by decantation
  3. customthe yellowish, oily residue was crystallized from methanol/ether
  4. customYield

Sources & evidence

ORD record
ord-a2b3fdab0f454883a7481ed903560e96
Source dataset
uspto-grants-1996_06
Patent number
US05525727

Reaction notes

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