Water → (3,4-Dinitrophenyl)-(4-methylpiperazin-1-yl)methanone

HRID 1639619Notes

Reaction equation

HRID 1639619 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[C:7]([OH:9])=O)([O-:3])=[O:2].[CH3:16][N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.CCN(CC)CC.O>O=S(Cl)Cl.C1COCC1>[N+:1]([C:4]1[CH:5]=[C:6]([C:7]([N:20]2[CH2:21][CH2:22][N:17]([CH3:16])[CH2:18][CH2:19]2)=[O:9])[CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 107093,4-Dinitrobenzoic acidHCID 531671-Methylpiperazine

Product 1

HCID 59139090(3,4-Dinitrophenyl)-(4-methylpiperazin-1-yl)methanoneYield 56.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
5 °C

Procedure

3,4-Dinitrobenzoic acid (50 g, 0.24 mol) was heated at reflux in SOCl2 (160 ml) for 6 hours. The mixture was then evaporated to dryness in vacuo. The product was dissolved in THF and cooled to 5° C. To this solution, N-methylpiperazine (26.2 ml, 0.24 mol) and Et3N (42 ml) were added dropwise as a solution in THF (50 ml). After stirring overnight at room temperature, the solution was poured into water (1.5 L) and stirred at approximately 5° C. for 0.5 hours. The solid precipitate which formed was collected and dried to give (3,4-dinitrophenyl)-(4-methylpiperazin-1-yl)-methanone (40 g) as a yellow solid.

Workup

  1. customThe mixture was then evaporated to dryness in vacuo
  2. dissolutionThe product was dissolved in THF
  3. stirringstirred at approximately 5° C. for 0.5 hours
  4. customThe solid precipitate which formed
  5. customwas collected
  6. customdried

Sources & evidence

ORD record
ord-576c8e37092e409284e510ca6662f5ce
Source dataset
uspto-grants-2012_02
Patent number
US08110573B2

Reaction notes

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