Ethanol → 3-((4-Methyl-1-piperazinyl)carbonyl)aniline

HRID 1261995Notes

Reaction equation

HRID 1261995 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-])=O)[CH:11]=2)=[O:9])[CH2:4][CH2:3]1.C(O)C.[H][H]>[Pd]>[NH2:16][C:12]1[CH:11]=[C:10]([C:8]([N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)=[O:9])[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 763411(4-Methylpiperazin-1-yl)(3-nitrophenyl)methanoneHCID 178418361HCID 178418361, compound

Product 1

HCID 167732183-((4-Methyl-1-piperazinyl)carbonyl)anilineYield 80.9%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

(4-Methyl-piperazin-1-yl)-(3-nitro-phenyl)-methanone (2.46 g, 9.87 mmol) was dissolved in Ethanol (30.0 mL, 514 mmol) and the solution was carefully added to a Parr vessel containing 10% Palladium on Carbon (0.750 g, 56.2 mmol) under nitrogen. The mixture was then placed on a Parr hydrogenation apparatus and was allowed to shake at 55 psi until uptake of hydrogen ceased. The catalyst was then filtered to afford 1.75 g of (3-Amino-phenyl)-(4-methyl-piperazin-1-yl)-methanone without further purification. (M+H)=220.6.

Workup

  1. additionthe solution was carefully added to a Parr vessel
  2. filtrationThe catalyst was then filtered

Sources & evidence

ORD record
ord-ac3feee0455f4bdebde533f434998222
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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