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

HRID 1728797Notes

Reaction equation

HRID 1728797 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:8][C:9](=[O:31])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:12][CH:11]=1.[CH3:32][I:33]>>[I-:33].[CH3:32][N+:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:8][C:9](=[O:31])[C:10]1[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 6328Methyl iodideHCID 10093859N-(2-Pyridinylmethyl)-4-(tetradecyloxy)benzamide

Product 1

HCID 100766471-Methyl-2-[[[4-(tetradecyloxy)benzoyl]amino]methyl]pyridinium iodide

Procedure

A mixture of 1.0 g of product from Example 4 and 7.33 ml of methyl iodide is heated, in a dark sealed tube, at 100°-120° C. for 22 hours. The cooled reaction mixture is concentrated in vacuo and recrystallized 2 times from methyl alcohol to give 1.15 g of the desired product as light yellow microneedles.

Workup

  1. temperatureis heated, in a dark sealed tube, at 100°-120° C. for 22 hours
  2. customThe cooled reaction mixture
  3. concentrationis concentrated in vacuo
  4. customrecrystallized 2 times from methyl alcohol

Sources & evidence

ORD record
ord-48a865b3a6d7484386a91d71f8746edd
Source dataset
uspto-grants-1994_07
Patent number
US05328921

Reaction notes

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