N,N'-Dimethylethylenediamine → 1,4-Dimethyl-3-(4-nitrophenyl)piperazin-2-one

HRID 1363484Notes

Reaction equation

HRID 1363484 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][NH:5][CH3:6].Br[CH:8]([C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)[C:9]([O:11]C)=O>C(O)C>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH3:6])[CH:8]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)[C:9]1=[O:11]

Participants

4

Reactant 2

HCID 8070N,N'-DimethylethylenediamineHCID 285582Methyl 2-bromo-2-(4-nitrophenyl)acetate

Product 1

HCID 576250981,4-Dimethyl-3-(4-nitrophenyl)piperazin-2-oneYield 89.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer was purged with nitrogen, charged with N1,N2-dimethylethane-1,2-diamine (1.61 g, 18.2 mmol), ethanol (5 mL) and 2 (500 mg, 1.82 mmol), and the reaction was stirred at room temperature for 1 h. After this time, the reaction mixture was evaporated under reduced pressure, and the resulting residue was purified by flash column chromatography to afford an 89% yield (404 mg) of 3 as a yellow oil: 1H NMR (500 MHz, DMSO-d6) δ 8.18 (d, 2H, J=8.5 Hz), 7.60 (d, 2H, J=8.5 Hz), 3.87 (s, 1H), 3.61 (td, 1H, J=12.0, 4.0 Hz), 3.26 (ddd, 1H, J=12.0, 4.0, 2.5 Hz), 3.02 (ddd, 1H, J=12.0, 4.0, 2.5 Hz), 2.84 (s, 3H), 2.64 (td, 1H, J=12.0, 4.0 Hz), 2.06 (s, 3H).

Workup

  1. customA 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. customwas purged with nitrogen
  3. customAfter this time, the reaction mixture was evaporated under reduced pressure
  4. customthe resulting residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-f9b6c40eb1ee4992b45b0f255af9a5a6
Source dataset
uspto-grants-2011_02
Patent number
US07884108B2

Reaction notes

Loading…