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

HRID 1358931Notes

Reaction equation

HRID 1358931 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].[H][H]>[Pd].C(O)C.O>[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

6

Reactant 2

HCID 18180062tert-Butyl 4-(2-methoxy-5-nitrophenyl)piperazine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 10686178Tert-butyl 4-(5-amino-2-methoxyphenyl)piperazine-1-carboxylateYield 99%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A slurry of 10% palladium on carbon (10 g) in a solution of 4-tert-butoxycarbonyl-1-(2-methoxy-5-nitrophenyl)piperazine (D2) (124.5 g) in ethanol (3.5L) and water (50 ml) was stirred with hydrogen at ambient temperature and atmospheric pressure for 18 h. The reaction mixture was filtered and the filtrate concentrated to afford the title compound (D3) as a gum (112 g, 99%). MH+ 308.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-6b3e017198c046ea952784515861017e
Source dataset
uspto-grants-2003_07
Patent number
US06599904B2

Reaction notes

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