1-(2-Difluoromethoxy-4-nitro-phenyl)-4-isopropyl-piperazine → 3-Difluoromethoxy-4-(4-isopropyl-piperazin-1-yl)-phenylamine

HRID 491623Notes

Reaction equation

HRID 491623 reaction equation
[F:1][CH:2]([F:22])[O:3][C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:5]=1[N:13]1[CH2:18][CH2:17][N:16]([CH:19]([CH3:21])[CH3:20])[CH2:15][CH2:14]1>CO.[Pd]>[F:22][CH:2]([F:1])[O:3][C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=1[N:13]1[CH2:18][CH2:17][N:16]([CH:19]([CH3:20])[CH3:21])[CH2:15][CH2:14]1

Participants

4

Reactant 1

HCID 690166651-(2-Difluoromethoxy-4-nitro-phenyl)-4-isopropyl-piperazine

Product 1

HCID 690156813-Difluoromethoxy-4-(4-isopropyl-piperazin-1-yl)-phenylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-(2-Difluoromethoxy-4-nitro-phenyl)-4-isopropyl-piperazine (Step B, 0.5 g, 1.9 mmol, 1.0 eq.) was dissolved in MeOH (10 mL). The atmosphere was replaced by argon. A catalytic amount of 10% Pd/C was added and the argon was replaced by a H2 atmosphere. The mixture was stirred for 16 h at RT at balloon pressure. The Pd/C was removed by filtration and the solvent was removed under vacuum to yield 3-difluoromethoxy-4-(4-isopropyl-piperazin-1-yl)-phenylamine. The crude material was used as is in the next step.

Workup

  1. customThe Pd/C was removed by filtration
  2. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-e9bfffd4019d430a82963c6b3c918385
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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