cis-3,5-Dimethyl-1-[4-(methyloxy)-3-nitrophenyl]piperazine → 5-(cis-3,5-Dimethyl-1-piperazinyl)-2-(methyloxy)aniline

HRID 130400Notes

Reaction equation

HRID 130400 reaction equation
[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([N+:17]([O-])=O)[CH:10]=2)[CH2:3]1>C(O)C.[Pd]>[CH3:8][C@H:6]1[NH:7][C@@H:2]([CH3:1])[CH2:3][N:4]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([CH:10]=2)[NH2:17])[CH2:5]1

Participants

4

Reactant 1

HCID 59007052cis-3,5-Dimethyl-1-[4-(methyloxy)-3-nitrophenyl]piperazine

Product 1

HCID 590070635-(cis-3,5-Dimethyl-1-piperazinyl)-2-(methyloxy)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of cis-3,5-dimethyl-1-[4-(methyloxy)-3-nitrophenyl]piperazine (D3) (2.65 g, 10 mmol) in ethanol (60 ml) containing palladium on charcoal (300 mg, 10% paste) was stirred under aone atmosphere of hydrogen gas overnight. The mixture was filtered through celite, the pad washed in ethanol and the combined ethanol solutions evaporated. The residue was purified by column chromatography (Biotage (SiO2) 100 g, dichloromethane to 1:10 2M ammonia in methanol:dichloromethane) to afford the title product (D4). MS (ES+) m/e 236 [M+H]+.

Workup

  1. filtrationThe mixture was filtered through celite
  2. washthe pad washed in ethanol
  3. customthe combined ethanol solutions evaporated
  4. customThe residue was purified by column chromatography (Biotage (SiO2) 100 g, dichloromethane to 1:10 2M ammonia in methanol:dichloromethane)

Sources & evidence

ORD record
ord-02667bc13b9349a1a9663f31c9975be8
Source dataset
uspto-grants-2008_06
Patent number
US07381728B2

Reaction notes

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