Methanol → (4-Aminophenyl)(4-methylpiperazin-1-yl)methanone

HRID 1261981Notes

Reaction equation

HRID 1261981 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=2)=[O:9])[CH2:4][CH2:3]1.CO.[H][H]>[Pd]>[NH2:16][C:13]1[CH:12]=[CH:11][C:10]([C:8]([N:5]2[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]2)=[O:9])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 716396(4-Methylpiperazin-1-yl)(4-nitrophenyl)methanoneHCID 178418361HCID 178418361, compound

Product 1

HCID 231408(4-Aminophenyl)(4-methylpiperazin-1-yl)methanoneYield 99.7%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

(4-Methyl-piperazin-1-yl)-(4-nitro-phenyl)-methanone (2.12 g, 8.51 mmol) was dissolved in Methanol (35 mL, 860 mmol) and the solution was carefully added to a Parr vessel containing 10% Palladium on Carbon (0.650 g, 48.7 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 1.86 g of (4-Amino-phenyl)-(4-methyl-piperazin-1-yl)-methanone without further purification. (M+H)=220.6. 1H NMR (400 MHz, DMSO, d6) δ 7.09 (d, 2H, J=8.41 Hz), 6.53 (d, 2H J=8.41 Hz), 5.48 (s, 2H), 3.46 (m, 4H), 2.28 (m, 4H), 2.17 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-733c82cdc92d4bc4a9b42801109bae0a
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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