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

HRID 1896381Notes

Reaction equation

HRID 1896381 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-d43b31158b7f4b6a851278066e337bd5
Source dataset
uspto-grants-2013_08
Patent number
US08518943B2

Reaction notes

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