Triethylamine → (2-Nitrophenyl){(2-oxo-4-propyl-pyrrolidin-1-yl)methyl}amine

HRID 1295818Notes

Reaction equation

HRID 1295818 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].F[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20].C(N(CC)CC)C>O1CCOCC1>[N+:19]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[NH:1][CH2:2][N:3]1[CH2:7][CH:6]([CH2:8][CH2:9][CH3:10])[CH2:5][C:4]1=[O:11])([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 738951-Fluoro-2-nitrobenzeneHCID 536292181-(Aminomethyl)-4-propylpyrrolidin-2-one

Product 1

HCID 58911262(2-Nitrophenyl){(2-oxo-4-propyl-pyrrolidin-1-yl)methyl}amine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1-aminomethyl-4-propyl-pyrrolidin-2-one a27 (1 eq, 17.09 mmol, 2.67 g), 2-fluoro-nitrobenzene (1 eq, 17.09 mmol, 2.411 g, 1.802 ml) and triethylamine (1.1 eq, 18.8 mmol, 1.902 g, 2.62 ml) in dioxane (20 ml) was refluxed 48 h. After cooling, the crude mixture was filtrated and the dioxane was distilled under vacuum. The residue was purified by preparative chromatography on reverse phase to give (2-nitrophenyl){(2-oxo-4-propyl-pyrrolidin-1-yl)methyl}amine a28 (2.747 g, 58%). LC/MS (MH+): 278.

Workup

  1. temperaturewas refluxed 48 h
  2. temperatureAfter cooling
  3. filtrationthe crude mixture was filtrated
  4. distillationthe dioxane was distilled under vacuum
  5. customThe residue was purified by preparative chromatography on reverse phase

Sources & evidence

ORD record
ord-760ff0532f4c4af2bc86bf0c174fbcc4
Source dataset
uspto-grants-2007_07
Patent number
US07244747B2

Reaction notes

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