Methyl iodide → 1-Methyl-4-(4-nitrophenyl)piperazine

HRID 1357478Notes

Reaction equation

HRID 1357478 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].[CH3:18]I>CN(C)C=O>[CH3:18][N:13]1[CH2:14][CH2:15][N:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)[CH2:11][CH2:12]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 804471-(4-Nitrophenyl)piperazine

Product 1

HCID 28251981-Methyl-4-(4-nitrophenyl)piperazineYield 90.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.04 g (5.0 mmol) of N-(4-nitrophenyl)piperazine was dissolved in 5 ml of dimethylformamide. Sodium hydride (0.24 g, 6.0 mmol) was added to the reaction mixture in three portions under nitrogen atmosphere and cooling over a period of 10 min. After 30 min of stirring, 0.31 ml (6.0 mmol) of methyl iodide was added dropwise to the reaction mixture at 0° C. Stirring was continued for 1 h at room temperature, the reaction mixture was then evaporated to dryness, and purified by silica gel chromatography (methylene chloride:methanol:triethylamine 94:5:1) to yield 1.0 g (90%) of 1-methyl-4-(4-nitrophenyl)piperazine.

Workup

  1. temperaturecooling over a period of 10 min
  2. stirringStirring
  3. waitwas continued for 1 h at room temperature
  4. customthe reaction mixture was then evaporated to dryness
  5. custompurified by silica gel chromatography (methylene chloride:methanol:triethylamine 94:5:1)

Sources & evidence

ORD record
ord-2ff8ef3c94a744bf90f339fd0226e3fb
Source dataset
uspto-grants-2003_07
Patent number
US06593324B2

Reaction notes

Loading…