tert-Butyl 4-(2-methoxy-5-nitrophenyl)piperazine-1-carboxylate → Tert-butyl 4-(5-amino-2-methoxyphenyl)piperazine-1-carboxylate

HRID 1710597Notes

Reaction equation

HRID 1710597 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([N+:20]([O-])=O)[CH:17]=[CH:16][C:15]=2[O:23][CH3:24])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([NH2:20])[CH:17]=[CH:16][C:15]=2[O:23][CH3:24])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 18180062tert-Butyl 4-(2-methoxy-5-nitrophenyl)piperazine-1-carboxylate

Product 1

HCID 10686178Tert-butyl 4-(5-amino-2-methoxyphenyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

33 g of 4-(2-Methoxy-5-nitro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (97.8 mmol) were dissolved in 450 mL of methanol. 3 g of 10% Pd/C were added at room temperature under nitrogen atmosphere, and the reaction mixture was hydrogenated for 4 h. The reaction mixture was filtered over Celite, the was solvent evaporated and the remaining residue was treated with 100 mL of diisopropylether. Once crystallization started, the solvent was removed under reduced pressure and the remaining product dried thoroughly. This material was used in subsequent steps without further purification.

Workup

  1. filtrationThe reaction mixture was filtered over Celite
  2. customthe was solvent evaporated
  3. additionthe remaining residue was treated with 100 mL of diisopropylether
  4. customOnce crystallization
  5. customthe solvent was removed under reduced pressure
  6. customthe remaining product dried thoroughly
  7. customThis material was used in subsequent steps without further purification

Sources & evidence

ORD record
ord-bcdd356ba6e74c68a46abd02d7f4913c
Source dataset
uspto-grants-2010_09
Patent number
US07790727B2

Reaction notes

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