Triethylamine → 2-Nitro-5-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]benzaldehyde

HRID 1649199Notes

Reaction equation

HRID 1649199 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:8][C:5]=1[CH:6]=[O:7])([O-:3])=[O:2].C(N(CC)CC)C.[CH3:25][O:26][C:27]1[CH:28]=[C:29]([CH:33]=[CH:34][C:35]=1[O:36][CH3:37])[C:30](Cl)=[O:31]>CN(C=O)C>[N+:1]([C:4]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:13][CH2:14][N:15]([C:30](=[O:31])[C:29]3[CH:33]=[CH:34][C:35]([O:36][CH3:37])=[C:27]([O:26][CH3:25])[CH:28]=3)[CH2:16][CH2:17]2)=[CH:8][C:5]=1[CH:6]=[O:7])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77070Veratroyl chlorideHCID 109893842-Nitro-5-piperazinylbenzaldehyde

Product 1

HCID 132363012-Nitro-5-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]benzaldehydeYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2-Nitro-5-piperazinylbenzaldehyde (5 g) was suspended in 50 ml of DMF and 6 ml of triethylamine was added to the suspension. A solution of 4.4 g of 3,4-dimethoxybenzoyl chloride in 20 ml of DMF was added dropwise thereto with ice cooling externally while stirring and the mixture was stirred at room temperature for 2 hours and poured into saturated saline and extracted with methylene chloride. After washing with water, the methylene chloride layer was dried over anhydrous sodium sulfate. Then, the solvent was removed by distillation and to the residue was added methyl alcohol and the mixture was heated and cooled and crystals which formed were recrystallized form DMF to give 4.5 g of 2-nitro-5-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]benzaldehyde, m.p. 196°-198° C., yellow crystal.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. additionpoured into saturated saline
  3. extractionextracted with methylene chloride
  4. washAfter washing with water
  5. dry with materialthe methylene chloride layer was dried over anhydrous sodium sulfate
  6. customThen, the solvent was removed by distillation and to the residue
  7. additionwas added methyl alcohol
  8. temperaturethe mixture was heated
  9. temperaturecooled
  10. customcrystals which formed
  11. customwere recrystallized form DMF

Sources & evidence

ORD record
ord-4d3ce01e8b304e919e6c0f6711038b89
Source dataset
uspto-grants-1983_11
Patent number
US04415572

Reaction notes

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