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

HRID 2410705Notes

Reaction equation

HRID 2410705 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>[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

3

Reactant 1

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

Product 1

HCID 231408(4-Aminophenyl)(4-methylpiperazin-1-yl)methanoneYield 98.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(4-Methylpiperazin-1-yl)(4-nitrophenyl)methanone (31.5 g, 126 mmol) was dissolved in methanol (150 ml) and transferred into a 500-ml PARR flask. The PARR flask was flushed with nitrogen, then 500 mg Pd/C (10% Pd) were added. The flask was flushed with nitrogen, then hydrogen, then shaken under a pressure of 50 psi of hydrogen for 17 hours. The mixture was filtered through CELITE®, the solid washed with MeOH and concentrated to give 27.2 g beige solid ((4-aminophenyl)(4-methylpiperazin-1-yl)methanone. MS (ESI) m/z 220 (M+H). 1H NMR (CDCl3) δ ppm 7.25 (d, 2H, J=7.6), 6.64 (d, 2H, J=7.6), 3.86 (bs, 2H), 3.63 (bs, 4H), 2.40 (bs, 4H), 2.30 (s, 3H).

Workup

  1. customThe PARR flask was flushed with nitrogen
  2. addition500 mg Pd/C (10% Pd) were added
  3. customThe flask was flushed with nitrogen
  4. filtrationThe mixture was filtered through CELITE®
  5. washthe solid washed with MeOH
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-14bf5e203a354a16b7ed76050c2a7857
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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