Tert-butyl 4-[4-(5-chloro-2-nitrophenoxy)phenyl]piperazine-1-carboxylate → Tert-butyl 4-[4-(2-amino-5-chlorophenoxy)phenyl]piperazine-1-carboxylate

HRID 1373261Notes

Reaction equation

HRID 1373261 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:28]([O-])=O)=[C:6]([CH:27]=1)[O:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)=[CH:10][CH:9]=1>[C].[Pd].C(OCC)(=O)C>[NH2:28][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:27][C:6]=1[O:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)=[CH:10][CH:9]=1

Participants

4

Reactant 1

HCID 17815432Tert-butyl 4-[4-(5-chloro-2-nitrophenoxy)phenyl]piperazine-1-carboxylate

Product 1

HCID 17815784Tert-butyl 4-[4-(2-amino-5-chlorophenoxy)phenyl]piperazine-1-carboxylateYield 76.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5% carbon-palladium (1.3 g) was added to an ethyl acetate (100 ml) solution of tert-butyl 4-[4-(5-chloro-2-nitrophenoxy)phenyl]piperazine-1-carboxylate (5.64 g, 13 mmols). The resulting mixture was hydrogenated at room temperature under atmospheric pressure. The catalyst was removed through filtration, and the filtrate was concentrated under reduced pressure. The residue was purified through silica gel column chromatography to give a crystal of tert-butyl 4-[4-(2-amino-5-chlorophenoxy)phenyl]piperazine-1-carboxylate (4.0 g, 76%).

Workup

  1. customwas hydrogenated at room temperature under atmospheric pressure
  2. customThe catalyst was removed through filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-71ddd2f371904a7991b237ae4ed29b1d
Source dataset
uspto-grants-2007_01
Patent number
US07160887B1

Reaction notes

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