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

HRID 1487151Notes

Reaction equation

HRID 1487151 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([SiH](CC)CC)C>CO.[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 2

HCID 12052TriethylsilaneHCID 763411(4-Methylpiperazin-1-yl)(3-nitrophenyl)methanone

Product 1

HCID 167732183-((4-Methyl-1-piperazinyl)carbonyl)anilineYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of (4-methylpiperazin-1-yl)(3-nitrophenyl)methanone (5.5 g, 22.06 mmol) in MeOH (50 ml) was added Pd—C (10%, 0.470 g) followed by triethylsilane (14.10 ml, 88 mmol) (slow addition) at RT. The reaction mixture was stirred at same temperature for 25 min and filtered through celite, washed with methanol (50 ml). The Filtrate was concentrated under vacuum to get the title product (4.11 g).

Workup

  1. filtrationfiltered through celite
  2. washwashed with methanol (50 ml)
  3. concentrationThe Filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-ec4c6f4b15364f1c9ba93fb08e74acc5
Source dataset
uspto-grants-2016_08
Patent number
US09428499B2

Reaction notes

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