Pyridine → N-(3-Pyridinylmethyl)-N-[4-(tetradecyloxy)phenyl]acetamide

HRID 248037Notes

Reaction equation

HRID 248037 reaction equation
[CH2:1]([O:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][CH2:23][C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].N1C=CC=CC=1.[C:36](Cl)(=[O:38])[CH3:37].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[N:26]1[CH:27]=[CH:28][CH:29]=[C:24]([CH2:23][N:22]([C:19]2[CH:18]=[CH:17][C:16]([O:15][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[CH:21][CH:20]=2)[C:36](=[O:38])[CH3:37])[CH:25]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 19015436N-[4-(Tetradecyloxy)phenyl]-3-pyridinemethanamine

Product 1

HCID 19015828N-(3-Pyridinylmethyl)-N-[4-(tetradecyloxy)phenyl]acetamideYield 96.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a room temperature solution of 2.49 g of product from Example 83, 1.27 ml of pyridine and 30 ml of methylene chloride is added, dropwise, 0.985 g of acetyl chloride. The reaction is stirred at room temperature for 1.5 hours, poured into saturated sodium bicarbonate and extracted with methylene chloride. The organic layer is washed with saturated sodium chloride, dried and concentrated in vacuo. The residue is purified by chromatography (silica gel: 95% ethyl acetate/hexane) to give 2.65 g of the desired product as a yellow oil.

Workup

  1. extractionextracted with methylene chloride
  2. washThe organic layer is washed with saturated sodium chloride
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by chromatography (silica gel: 95% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-6847bf3602834032b6243affd4842edc
Source dataset
uspto-grants-1993_05
Patent number
US05208247

Reaction notes

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