5-(1-Methyl-1,2,3,6-tetrahydropyridin-4-yl)-2-nitropyridine → 5-(1-Methylpiperidin-4-yl)pyridin-2-amine

HRID 1022013Notes

Reaction equation

HRID 1022013 reaction equation
[CH3:1][N:2]1[CH2:7][CH:6]=[C:5]([C:8]2[CH:9]=[CH:10][C:11]([N+:14]([O-])=O)=[N:12][CH:13]=2)[CH2:4][CH2:3]1>[Pd].CO>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:9]=[CH:10][C:11]([NH2:14])=[N:12][CH:13]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 580442465-(1-Methyl-1,2,3,6-tetrahydropyridin-4-yl)-2-nitropyridine

Product 1

HCID 580438205-(1-Methylpiperidin-4-yl)pyridin-2-amineYield 92.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A 250-mL single-neck round-bottomed flask was purged with nitrogen and charged with 232b (2.0 g, 9.0 mmol), 10% palladium on carbon (50% wet, 200 mg), and methanol (40 mL). The flask was evacuated, charged with hydrogen gas, and stirred under hydrogen at room temperature for 12 h. The 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 232c (1.6 g, 92.5%), which was used directly in the next step without further purification. MS-ESI: [M+H]+ 192

Workup

  1. customA 250-mL single-neck round-bottomed flask was purged with nitrogen
  2. customThe flask was evacuated
  3. additioncharged with hydrogen gas
  4. customThe hydrogen 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-b06d6546269245f8a49d53fe3c485749
Source dataset
uspto-grants-2014_05
Patent number
US08716274B2

Reaction notes

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