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

HRID 2358248Notes

Reaction equation

HRID 2358248 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%).

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-3997d36f7d874e4b9248bdb0b86d1dbc
Source dataset
uspto-grants-2010_07
Patent number
US07763644B2

Reaction notes

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