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

HRID 1021901Notes

Reaction equation

HRID 1021901 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-4c6ddb8d24d0459dadd7a0d3c5c046e8
Source dataset
uspto-grants-2014_05
Patent number
US08716274B2

Reaction notes

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