3-(4-Pyridinyl)-2-propenoic acid → 3-(Piperidin-4-yl)propanoic acid

HRID 1789785Notes

Reaction equation

HRID 1789785 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=[CH:8][C:9]([OH:11])=[O:10])=[CH:3][CH:2]=1.[H][H]>O.N.[Ru]>[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][C:9]([OH:11])=[O:10])[CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 953033-(4-Pyridinyl)-2-propenoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 15208063-(Piperidin-4-yl)propanoic acidYield 100%

Reagents, catalysts & solvents 3

HCID 23950RutheniumCatalystHCID 222AmmoniaSolventHCID 962WaterSolvent

Procedure

A solution of 3-pyridin4-yl-acrylic acid (4.20 g, 28.0 mmol) in water (50 mL) and ammonia (aq, 25%, 4 mL) was hydrogenated at 60 bar in a high pressure steel autoclave in presence of ruthenium (5% on alumina, 439 mg). When hydrogen pressure remained constant (3 days) the catalyst was removed from the reaction mixture by filtration. The catalyst was washed with ethanol and water, and the ethanol was removed from the solution on a rotavapor and the aqueous solution was freeze dried to give 3-piperidin4-yl-propionic acid (4.30 g, 100%).

Workup

  1. custom(3 days)
  2. customwas removed from the reaction mixture by filtration
  3. washThe catalyst was washed with ethanol and water
  4. customthe ethanol was removed from the solution on a rotavapor
  5. customdried

Sources & evidence

ORD record
ord-fa704ecb2dbe442f93a503e20069bbcd
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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