Pyridine → N-Acetyl-N-(2-pyridinylmethyl)-4-(tetradecyloxy)benzamide

HRID 1728792Notes

Reaction equation

HRID 1728792 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.[C:32](OC(=O)C)(=[O:34])[CH3:33].N1C=CC=CC=1>CN(C)C1C=CN=CC=1.O>[C:32]([N:8]([CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[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)(=[O:34])[CH3:33]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 10093859N-(2-Pyridinylmethyl)-4-(tetradecyloxy)benzamide

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

A mixture of 2.0 g of product from Example 4, 8.9 ml acetic anhydride, 0.0863 g 4-dimethylaminopyridine and 30 ml pyridine is heated at reflux temperature for 23 hours, cooled, poured into 150 ml of water and extracted with methylene chloride. The organic layer is washed with saturated sodium chloride, dried and concentrated in vacuo. The residue is purified by column chromatogaphy (silica ge1:15-20% ethyl acetate/hexane) to give 1.4 g of the desired product as light yellow crystals.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 23 hours
  3. temperaturecooled
  4. extractionextracted with methylene chloride
  5. washThe organic layer is washed with saturated sodium chloride
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by column chromatogaphy (silica ge1:15-20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d3fdd6ae02084b84879dab84c28d750c
Source dataset
uspto-grants-1994_07
Patent number
US05328921

Reaction notes

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