tert-Butyl 4-(5-nitropyridin-2-yl)piperazine-1-carboxylate → tert-Butyl 4-(5-aminopyridin-2-yl)piperazine-1-carboxylate

HRID 592832Notes

Reaction equation

HRID 592832 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=[N:8][CH:9]=1)([O-])=O>[Pd].CO>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=[N:8][CH:9]=1

Participants

4

Reactant 1

HCID 16217943tert-Butyl 4-(5-nitropyridin-2-yl)piperazine-1-carboxylate

Product 1

HCID 17999304tert-Butyl 4-(5-aminopyridin-2-yl)piperazine-1-carboxylateYield 91.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A 250-mL round-bottomed flask was purged with nitrogen and charged with 197a (4.0 g, 13.0 mmol), 10% palladium on carbon (10% wet, 500 mg), and methanol (130 mL). The flask was evacuated, charged with hydrogen gas, and stirred at room temperature for 15 h. Hydrogen was then evacuated and nitrogen was charged to the flask. The catalyst was removed by filtration through a pad of CELITE® and the filtrate was concentrated under reduced pressure to afford 197b (3.3 g, 91%). MS-ESI: [M+H]+ 279

Workup

  1. customA 250-mL round-bottomed flask was purged with nitrogen
  2. customThe flask was evacuated
  3. additioncharged with hydrogen gas
  4. customHydrogen was then evacuated
  5. additionnitrogen was charged to the flask
  6. customThe catalyst was removed by filtration through a pad of CELITE®
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-67f7a9ad04d9461381b6717d9f0bba60
Source dataset
uspto-grants-2016_01
Patent number
US09238655B2

Reaction notes

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