2-[(1-Methyl-4-piperidinyl)oxy]-5-nitropyridine → 6-[(1-methylpiperidin-4-yl)oxy]pyridin-3-amine

HRID 1512104Notes

Reaction equation

HRID 1512104 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][N:10]=2)[CH2:4][CH2:3]1.[H][H]>CO.[Pd]>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([O:8][C:9]2[N:10]=[CH:11][C:12]([NH2:15])=[CH:13][CH:14]=2)[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 529048992-[(1-Methyl-4-piperidinyl)oxy]-5-nitropyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 283176056-[(1-methylpiperidin-4-yl)oxy]pyridin-3-amineYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-(1-Methylpiperidin-4-yloxy)-5-nitropyridine (100 mg, 0.42 mmol) was dissolved in 5 mL of methanol and placed under a nitrogen atmosphere. A catalytic amount of 10% palladium on carbon was added and a hydrogen balloon connected to the reaction flask. The flask was flushed five times with hydrogen and stirred at room temperature under hydrogen atmosphere. The solid was filtered and washed with methanol. The filtrate was evaporated under reduced pressure to yield 6-(1-methylpiperidin-4-yloxy)pyridin-3-amine as a brown solid (85 mg, 98%). LC/MS (m/z): 208.2 (MH+), Rt 0.34 minutes.

Workup

  1. customThe flask was flushed five times with hydrogen
  2. filtrationThe solid was filtered
  3. washwashed with methanol
  4. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-437ff5c4d9ef46d6a051640977ac3941
Source dataset
uspto-grants-2012_07
Patent number
US08217035B2

Reaction notes

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