Tert-butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate → tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate

HRID 1919000Notes

Reaction equation

HRID 1919000 reaction equation
[N+:1]([C:4]1[N:9]=[CH:8][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)=[CH:6][CH:5]=1)([O-])=O>[Pd].C(O)C>[NH2:1][C:4]1[N:9]=[CH:8][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)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 11243758Tert-butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate

Product 1

HCID 11737525tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylateYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A 500-mL bottle was purged with nitrogen and charged with tert-butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate (3.1 g, 10 mmol), 10% palladium on carbon (50% wet, 1 g) and ethanol (100 mL). The bottle was evacuated, charged with hydrogen gas, and stirred for 16 h at room temperature. The hydrogen was then evacuated and nitrogen charged into the bottle. The catalyst was removed by filtration through a pad of Celite and the filtrate concentrated under reduced pressure to afford tert-butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate (2.7 g, 97%). MS: [M+H]+ 279

Workup

  1. customA 500-mL bottle was purged with nitrogen
  2. customThe bottle was evacuated
  3. additioncharged with hydrogen gas
  4. customThe hydrogen was then evacuated
  5. additionnitrogen charged into the bottle
  6. customThe catalyst was removed by filtration through a pad of Celite
  7. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-5430f715f3894e7b8e0b2f6a497f576d
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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