Sodium hydride → N-(3-Pyridinylmethyl)-N-[[4-(tetradecyloxy)phenyl]methyl]acetamide

HRID 247981

Reaction equation

HRID 247981 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][CH:27]=[C:26]([CH2:30][NH:31][C:32](=[O:34])[CH3:33])[CH:25]=1.[H-].[Na+]>O1CCCC1>[N:24]1[CH:29]=[CH:28][CH:27]=[C:26]([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:25]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27352253-(Acetamidomethyl)pyridineHCID 100228401-(Bromomethyl)-4-(tetradecyloxy)benzene

Product 1

HCID 10026896N-(3-Pyridinylmethyl)-N-[[4-(tetradecyloxy)phenyl]methyl]acetamideYield 41.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound is prepared by the procedure of Example 27 using 1.1 g of product from Example 20, 0.431 g of product from Example 14, 0.145 g of washed 50% sodium hydride and 12 ml of tetrahydrofuran. The reaction is stirred at room temperature for 21 hours followed by heating at reflux temperature for 51/2 hours. The residue is purified by column chromatography (silica gel: 5% methyl alcohol/ethyl acetate) to give 0.535 g of the desired product. The spectral data indicates the presence of 2 rotomers.

Workup

  1. temperatureby heating
  2. temperatureat reflux temperature for 51/2 hours
  3. customThe residue is purified by column chromatography (silica gel: 5% methyl alcohol/ethyl acetate)

Sources & evidence

ORD record
ord-7ecd094e02f849b89499a502fba3fc5d
Source dataset
uspto-grants-1993_05
Patent number
US05208247

Linked notes

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