(4-Methylpiperazin-1-yl)(4-nitrophenyl)methanone → (4-Aminophenyl)(4-methylpiperazin-1-yl)methanone

HRID 517422Notes

Reaction equation

HRID 517422 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.[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

4

Reactant 1

HCID 716396(4-Methylpiperazin-1-yl)(4-nitrophenyl)methanone

Product 1

HCID 231408(4-Aminophenyl)(4-methylpiperazin-1-yl)methanoneYield 89.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (4-Methyl-piperazin-1-yl)-(4-nitro-phenyl)-methanone (14 g, 0.05623 mol) in MeOH (100 mL) was added Pd/C 10% (1.4 g) in portions and the Parr reaction vessel was purged with nitrogen for 10 min. reaction vessel was fixed in Parr shaker at 60 psi pressure for 3 h. The reaction mixture was filtered through the Celite® pad and the filtrate was concentrated under reduced pressure to afford the title compound [11 g, 89%]; LC-MS (ESI): Calculated mass 219.1; Observed mass: 220.1 [M+H]+ (RT: 0.16 min).

Workup

  1. customthe Parr reaction vessel
  2. customwas purged with nitrogen for 10 min.
  3. customreaction vessel
  4. filtrationThe reaction mixture was filtered through the Celite® pad
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-afbc65f573fb4bd087bcbe703a5efcea
Source dataset
uspto-grants-2015_08
Patent number
US09115092B2

Reaction notes

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