1-Boc-4-(2-nitrophenyl)piperazine → tert-Butyl 4-(2-aminophenyl)piperazine-1-carboxylate

HRID 228071Notes

Reaction equation

HRID 228071 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1)([O-])=O>CCO.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1

Participants

4

Reactant 1

HCID 219352101-Boc-4-(2-nitrophenyl)piperazine

Product 1

HCID 2795530tert-Butyl 4-(2-aminophenyl)piperazine-1-carboxylateYield 99.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Into a 500 mL round bottomed flask equipped with magnetic stirring was added tert-butyl 4-(2-nitrophenyl)piperazinecarboxylate (5.0 g, 16 mmol) in 95% EtOH (250 mL), and 10% Pd/C (2.0 g, 1.9 mmol) (Aldrich). The flask was equipped with a balloon filled with H2, and the reaction was stirred for 18 h. After filtering through a pad of Celite®, the crude material was concentrated in vacuo to afford the desired compound (4.4 g). MS (ESI, pos. ion) m/z: 278 (M+H), (ESI, neg. ion) m/z: 276 (M−H). Calc'd for C15H23N3O2: 277.18.

Workup

  1. customInto a 500 mL round bottomed flask equipped
  2. customThe flask was equipped with a balloon
  3. additionfilled with H2
  4. stirringthe reaction was stirred for 18 h
  5. filtrationAfter filtering through a pad of Celite®
  6. concentrationthe crude material was concentrated in vacuo

Sources & evidence

ORD record
ord-64006f00f32e4129a46544abc1a97b85
Source dataset
uspto-grants-2009_07
Patent number
US07560460B2

Reaction notes

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