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

HRID 1262234Notes

Reaction equation

HRID 1262234 reaction equation
CO[C:3](=[O:15])[CH:4](Br)[C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1.[CH3:16][NH:17][CH2:18][CH2:19][NH:20][CH3:21]>C(O)C>[CH3:16][N:17]1[CH2:18][CH2:19][N:20]([CH3:21])[CH:4]([C:5]2[CH:6]=[CH:7][C:8]([N+:11]([O-:13])=[O:12])=[CH:9][CH:10]=2)[C:3]1=[O:15]

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 90.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Bromo-(4-nitro-phenyl)-acetic acid methyl ester (547 mg, 2.00 mmol) was dissolved in ethanol (5.50 mL) and N,N′-dimethyl-ethane-1,2-diamine (1.07 mL, 9.98 mmol) was added. The reaction was stirred at room temperature for 30 minutes and then concentrated under reduced pressure. Purification by silica gel chromatography using a gradient of 0-10% MeOH/DCM as the eluting solvent to obtain 1,4-dimethyl-3-(4-nitro-phenyl)-piperazin-2-one as an orange solid (450 mg, 90%). m.p.=99-102° C.; LCMS (m/e) 250 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 8.19 (d, 2H, J=8.6 Hz), 7.61 (d, 2H, J=8.6 Hz), 3.83 (s, 1H), 3.81-3.70 (m, 1H), 3.26-3.18 (m, 1H), 3.08-3.00 (m, 1H), 2.97 (s, 3H), 2.78-2.68 (m, 1H), 2.18 (s, 3H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-7c3c3bf3014748779c902d7b089f952f
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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