2-(5-Methyl-3-trifluoromethyl-pyrazol-1-yl)-1-[4-(3-nitro-phenyl)-piperazin-1-yl]-ethanone → 1-[4-(3-Amino-phenyl)-piperazin-1-yl]-2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-ethanone

HRID 403366Notes

Reaction equation

HRID 403366 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-])=O)[CH:17]=3)[CH2:12][CH2:11]2)=[O:9])[N:5]=[C:4]([C:25]([F:28])([F:27])[F:26])[CH:3]=1>C(O)C.[Pd]>[NH2:22][C:18]1[CH:17]=[C:16]([N:13]2[CH2:12][CH2:11][N:10]([C:8](=[O:9])[CH2:7][N:6]3[C:2]([CH3:1])=[CH:3][C:4]([C:25]([F:28])([F:27])[F:26])=[N:5]3)[CH2:15][CH2:14]2)[CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 1

HCID 682800452-(5-Methyl-3-trifluoromethyl-pyrazol-1-yl)-1-[4-(3-nitro-phenyl)-piperazin-1-yl]-ethanone

Product 1

HCID 682800911-[4-(3-Amino-phenyl)-piperazin-1-yl]-2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-ethanoneYield 99.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a suspension of (2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-1-[4-(3-nitro-phenyl)-piperazin-1-yl]-ethanone (1.03 g, 2.59 mmol) in ethanol (50 mL) is added 10% Pd/C (100 mg). The reaction mixture is stirred under hydrogen (1 atm) for 2 h, and then filtered over Celite, washed with ethanol, and evaporated under pressure to give 1-[4-(3-amino-phenyl)-piperazin-1-yl]-2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-ethanone (0.95 g, 99%). 1H-NMR (400 MHz, DMSO-d6): δ=2.21 (s, 3H), 3.01-3.09 (m, 2H), 3.11-3.18 (m, 2H), 3.53-3.69 (m, 4H), 4.90 (br, 2H), 5.30 (s, 2H), 6.06-6.11 (m, 1H), 6.13-6.20 (m, 2H), 6.50 (s, 1H), 6.85-6.91 (m, 1H). MS: m/z=368 (M+1).

Workup

  1. filtrationfiltered over Celite
  2. washwashed with ethanol
  3. customevaporated under pressure

Sources & evidence

ORD record
ord-a8255181a90f48d582d70d0918ea3715
Source dataset
uspto-grants-2014_06
Patent number
US08748432B2

Reaction notes

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