1-Methyl-4-[[3-nitro-5-(trifluoromethyl)phenyl]methyl]piperazine → 3-((4-Methylpiperazin-1-yl)methyl)-5-(trifluoromethyl)aniline

HRID 2200148Notes

Reaction equation

HRID 2200148 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[C:11]([N+:19]([O-])=O)[CH:10]=2)[CH2:4][CH2:3]1>CO.[Pd]>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:10]=[C:11]([CH:12]=[C:13]([C:15]([F:18])([F:16])[F:17])[CH:14]=2)[NH2:19])[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 589023661-Methyl-4-[[3-nitro-5-(trifluoromethyl)phenyl]methyl]piperazine

Product 1

HCID 231550523-((4-Methylpiperazin-1-yl)methyl)-5-(trifluoromethyl)anilineYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Add Pd/C (10%, 200 mg) to the solution of 1-methyl-4-(3-nitro-5-(trifluoromethyl)benzyl)piperazine (812 mg, 2.68 mmol) in methanol (15 mL), flush with H2, stir under hydrogen atmosphere for 16 hrs at room temperature. Filter and concentrate the filtrate to give the crude product (732 mg, 100%). MS: (M+1): 273.0.

Workup

  1. customflush with H2
  2. filtrationFilter
  3. concentrationconcentrate the filtrate

Sources & evidence

ORD record
ord-b5973325894f445c9038746304f113c1
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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