Sodium hydride → N-(4-Pyridinylmethyl)-N-[[4-(tetradecyloxy)phenyl]methyl]acetamide

HRID 247985

Reaction equation

HRID 247985 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:5][CH:4]=1.[N:24]1[CH:29]=[CH:28][C:27]([CH2:30][NH:31][C:32](=[O:34])[CH3:33])=[CH:26][CH:25]=1.[H-].[Na+]>O1CCCC1>[N:24]1[CH:29]=[CH:28][C:27]([CH2:30][N:31]([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:5][CH:4]=2)[C:32](=[O:34])[CH3:33])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 289830N-(4-Pyridinylmethyl)acetamideHCID 100228401-(Bromomethyl)-4-(tetradecyloxy)benzene

Product 1

HCID 10095404N-(4-Pyridinylmethyl)-N-[[4-(tetradecyloxy)phenyl]methyl]acetamideYield 28.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound is prepared by the procedure of Example 27 using 2.55 g of product from Example 20, 0.999 g of product from Example 15, 0.319 g of washed 50% sodium hydride and 30 ml of tetrahydrofuran. The reaction is stirred at room temperature for 18 hours, heated at reflux temperature for 24 hours; followed by stirring at room temperature for an additional 48 hours. The residue is purified by column chromatography (silica gel: 5% methyl alcohol/ethyl acetate) to give 0.862 g of the desired product. The spectral data indicates the presence of 2 rotomers.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 24 hours
  3. stirringby stirring at room temperature for an additional 48 hours
  4. customThe residue is purified by column chromatography (silica gel: 5% methyl alcohol/ethyl acetate)

Sources & evidence

ORD record
ord-c0e7154a20b54b938f00db7f5da9dcc4
Source dataset
uspto-grants-1993_05
Patent number
US05208247

Linked notes

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