Tetrahydrofuran → N-Acetyl-3,4-bis(heptyloxy)-N-(2-pyridinylmethyl)benzamide

HRID 248015Notes

Reaction equation

HRID 248015 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:12](Cl)=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[H-].[Na+].[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH2:34][NH:35][C:36](=[O:38])[CH3:37].O1CCCC1>O>[C:36]([N:35]([CH2:34][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][N:28]=1)[C:12](=[O:13])[C:11]1[CH:15]=[CH:16][C:17]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[C:9]([O:8][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[CH:10]=1)(=[O:38])[CH3:37]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 5084090N-(pyridin-2-ylmethyl)acetamideHCID 190151863,4-Bis(heptyloxy)benzoyl chloride

Product 1

HCID 10367999N-Acetyl-3,4-bis(heptyloxy)-N-(2-pyridinylmethyl)benzamideYield 44.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound is prepared by the procedure of Example 27 using 5.0 g of product from Example 111, 0.683 g of washed 50% sodium hydride, 2.14 g of product from Example 12 and 100 ml of dry tetrahydrofuran. The reaction is stirred at room temperature for 1 hour, heated at reflux temperature for 18 hours and cooled to room temperature. The mixture is poured into water, extracted with chloroform and concentrated in vacuo. The residue is purified by column chromatography (silica gel: 15-30% ethyl acetate/hexane) to give 2.93 g of the desired product.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 18 hours
  3. temperaturecooled to room temperature
  4. extractionextracted with chloroform
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by column chromatography (silica gel: 15-30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-0bd7858628244defa554613b343fb739
Source dataset
uspto-grants-1993_05
Patent number
US05208247

Reaction notes

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