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

HRID 1036205Notes

Reaction equation

HRID 1036205 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.[H][H]>[Pd].CO>[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

5

Reactant 2

HCID 11243758Tert-butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 11737525tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a round-bottom flask was added tert-butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate 125-3 (3.4 g, 11 mmol), Pd/C (0.5 g) and methanol (100 mL). The reaction was stirred for 4 hours under hydrogen atmosphere by attaching a hydrogen balloon. The reaction was flushed with nitrogen and the solid was removed by filtration. The solvent was removed by rotary evaporation to give tert-butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate 125-4 as purple solid. MS m/z 279.2 (M+1).

Workup

  1. customThe reaction was flushed with nitrogen
  2. customthe solid was removed by filtration
  3. customThe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-21f3a06813814df79f1b27c79b2c0b4a
Source dataset
uspto-grants-2013_10
Patent number
US08546396B2

Reaction notes

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