Benzyl Bromide → 2-[[Acetyl[4-(tetradecyloxy)benzoyl]amino]methyl]-1-(phenylmethyl)pyridinium bromide

HRID 247919Notes

Reaction equation

HRID 247919 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].[CH2:35]([Br:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C(#N)C>[Br-:42].[C:1]([N:4]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N+:30]=1[CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[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

4

Reactant 2

HCID 7498Benzyl BromideHCID 11754296N-Acetyl-N-(2-pyridinylmethyl)-4-(tetradecyloxy)benzamide

Product 1

HCID 104617652-[[Acetyl[4-(tetradecyloxy)benzoyl]amino]methyl]-1-(phenylmethyl)pyridinium bromideYield 50.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 0.75 g of product from Example 5, 0.412 g of benzyl bromide and 3 ml of acetonitrile is stirred at room temperature for 17.5 hours then heated, in a sealed tube, at 100° C. for 21.25 hours. The cooled reaction mixture is concentrated in vacuo and the residue purified by column chromatography (silica gel: 10% methyl alcohol/chloroform) to give 0.515 g of the desired product.

Workup

  1. temperaturethen heated, in a sealed tube, at 100° C. for 21.25 hours
  2. customThe cooled reaction mixture
  3. concentrationis concentrated in vacuo
  4. customthe residue purified by column chromatography (silica gel: 10% methyl alcohol/chloroform)

Sources & evidence

ORD record
ord-278fac69d2954beea6dae9c36d44ea40
Source dataset
uspto-grants-1993_05
Patent number
US05208247

Reaction notes

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