Triethylamine → 1-{[(3-Nitropyridin-2-yl)amino]methyl}-4-propylpyrrolidin-2-one

HRID 1924244Notes

Reaction equation

HRID 1924244 reaction equation
[NH2:1][CH2:2][N:3]1[CH2:7][CH:6]([CH2:8][CH2:9][CH3:10])[CH2:5][C:4]1=[O:11].Cl[C:13]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[CH:15][N:14]=1.C(N(CC)CC)C>O1CCOCC1>[N+:19]([C:18]1[C:13]([NH:1][CH2:2][N:3]2[CH2:7][CH:6]([CH2:8][CH2:9][CH3:10])[CH2:5][C:4]2=[O:11])=[N:14][CH:15]=[CH:16][CH:17]=1)([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 796132-Chloro-3-nitropyridineHCID 536292181-(Aminomethyl)-4-propylpyrrolidin-2-one

Product 1

HCID 577430171-{[(3-Nitropyridin-2-yl)amino]methyl}-4-propylpyrrolidin-2-oneYield 53%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1-(aminomethyl)-4-propylpyrrolidin-2-one x76 (1 eq, 17.09 mmol, 2.67 g), 2-chloro-3-nitropyridine (1 eq, 17.09 mmol, 2.709 g) and triethylamine (1.1 eq, 18.8 mmol, 1.902 g, 2.62 ml) in dioxane (20 ml) is refluxed 48 h. After cooling, the crude mixture is filtrated and the dioxane is distilled under vacuum. The residue is purified by preparative chromatography to afford 2.5 g of 1-{[(3-nitropyridin-2-yl)amino]methyl}-4-propylpyrrolidin-2-one x77.

Workup

  1. temperatureis refluxed 48 h
  2. temperatureAfter cooling
  3. filtrationthe crude mixture is filtrated
  4. distillationthe dioxane is distilled under vacuum
  5. customThe residue is purified by preparative chromatography

Sources & evidence

ORD record
ord-4da99e7033624968850423c1afd5281a
Source dataset
uspto-grants-2012_05
Patent number
US08178533B2

Reaction notes

Loading…