2,4-Dinitrobenzoic acid → (2,4-Dinitrophenyl)(4-methylpiperazin-1-yl)methanone

HRID 2108144

Reaction equation

HRID 2108144 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=O)([O-:3])=[O:2].[CH3:16][N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.P(Cl)(Cl)(Cl)=O.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.C(N(CC)CC)C>[CH3:16][N:17]1[CH2:22][CH2:21][N:20]([C:6](=[O:8])[C:5]2[CH:9]=[CH:10][C:11]([N+:13]([O-:15])=[O:14])=[CH:12][C:4]=2[N+:1]([O-:3])=[O:2])[CH2:19][CH2:18]1

Participants

7

Reactant 4

HCID 118802,4-Dinitrobenzoic acidHCID 24813Phosphorus oxychlorideHCID 531671-MethylpiperazineHCID 516892Sodium Bicarbonate

Product 1

HCID 4090619(2,4-Dinitrophenyl)(4-methylpiperazin-1-yl)methanoneYield 54.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
80 °C

Procedure

To a slurry of 212.0 g of 2,4-dinitrobenzoic acid in 1400 ml of toluene was added with agitation 101.0 g of triethylamine, followed by 122.7 g of N-methylpiperazine. Next 75.7 g of phosphorus oxychloride was added dropwise at such a rate to maintain the reaction temperature below 90° C. The mixture was refluxed for 5 hrs. cooled to 80° C., and poured slowly into 1000 ml of aqueous 5% NaHCO3 solution with stirring. The precipitate was filtered, washed with water and recrystallized from hot methanol to yield 161 g of N1 -methyl-N4 -(2,4-dinitrobenzoyl)- piperazine, mp 130°-132° C.

Workup

  1. temperatureto maintain the reaction temperature below 90° C
  2. temperatureThe mixture was refluxed for 5 hrs
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. customrecrystallized from hot methanol

Sources & evidence

ORD record
ord-648c22ff6e9d47bf80ef0ac41f1f532f
Source dataset
uspto-grants-1990_06
Patent number
US04937306

Linked notes

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