Methyl iodide → 2-[[Acetyl[4-(tetradecyloxy)benzoyl]amino]methyl]-1-methylpyridinium iodide

HRID 247918Notes

Reaction equation

HRID 247918 reaction equation
[C:1]([N:4]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=1)[C:5](=[O:27])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:8][CH:7]=1)(=[O:3])[CH3:2].[CH3:35][I:36]>>[I-:36].[C:1]([N:4]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N+:30]=1[CH3:35])[C:5](=[O:27])[C:6]1[CH:7]=[CH:8][C:9]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:10][CH:11]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 6328Methyl iodideHCID 11754296N-Acetyl-N-(2-pyridinylmethyl)-4-(tetradecyloxy)benzamide

Product 1

HCID 98518222-[[Acetyl[4-(tetradecyloxy)benzoyl]amino]methyl]-1-methylpyridinium iodide

Conditions

Temperature
115 °C

Procedure

A mixture of 0.808 g of product from Example 5 and 5.39 ml of methyl iodide is heated, in a sealed dark tube, at 115° C. for 23 hours. The cooled reaction mixture is concentrated in vacuo and the residue purified by column chromatography (silica gel: 20% methyl alcohol/chloroform) to give 0.63 g of the desired product as cream crystals.

Workup

  1. customThe cooled reaction mixture
  2. concentrationis concentrated in vacuo
  3. customthe residue purified by column chromatography (silica gel: 20% methyl alcohol/chloroform)

Sources & evidence

ORD record
ord-28133839db2e482d86024a38cd18449a
Source dataset
uspto-grants-1993_05
Patent number
US05208247

Reaction notes

Loading…