Acetic Acid → Methyl 5-methylpiperidine-3-carboxylate

HRID 1019661Notes

Reaction equation

HRID 1019661 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].CC(O)=O>CCO.[Pd]>[CH3:1][CH:2]1[CH2:3][NH:4][CH2:5][CH:6]([C:7]([O:9][CH3:10])=[O:8])[CH2:11]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 256308Methyl 5-methylpyridine-3-carboxylate

Product 1

HCID 18404439Methyl 5-methylpiperidine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a reaction vessel containing methyl 5-methylnicotinate (Alfa Aesar, 1 g, 6.62 mmol) in EtOH (12.03 mL) was added AcOH (1.203 mL). The reaction vessel was purged with nitrogen gas (3×) and 10 weight percent palladium on carbon (0.5 g, 4.70 mmol) was added. The reaction vessel was then purged with hydrogen (balloon, 1 atm) (3×) and maintained under hydrogen while stirring. After 48 hours, the reaction was filtered over Celite® brand filter aid and concentrated under reduced pressure to give methyl 5-methylpiperidine-3-carboxylate. ESI-MS M+H 158.0.

Workup

  1. additionwas added
  2. customThe reaction vessel was then purged with hydrogen (balloon, 1 atm) (3×)
  3. temperaturemaintained under hydrogen
  4. filtrationthe reaction was filtered over Celite® brand
  5. filtrationfilter aid
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8e450a9093df4983a11c49fc3ad822fd
Source dataset
uspto-grants-2014_05
Patent number
US08716281B2

Reaction notes

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