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

HRID 1043775Notes

Reaction equation

HRID 1043775 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): 2082 (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-f20905eac33e4850a12cf399388b048b
Source dataset
uspto-grants-2013_10
Patent number
US08563549B2

Reaction notes

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