4-Pyridinepropanol → 4-Piperidinepropanol

HRID 2108728Notes

Reaction equation

HRID 2108728 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9][OH:10])=[CH:3][CH:2]=1.[H][H]>C(O)(=O)C.[Pd]>[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][CH2:9][OH:10])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 729234-PyridinepropanolHCID 178418361HCID 178418361, compound

Product 1

HCID 814974-Piperidinepropanol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

4-Pyridinepropanol (10.0 g, 73 mmol) was dissolved in glacial acetic acid (50 mL). 10% Palladium on carbon (1.1 g) was added and the mixture hydrogenated under 50 psi hydrogen gas for 6 days. The mixture was filtered through Celite and the solvent removed by rotary evaporation. The crude product 3-piperidin-4-yl-propan-1-ol (acetic acid salt) was used as obtained. 1H NMR (500 MHz, CDCl3) □ 6.3 (br), 3.65 (2H, t), 3.36 (2H, m), 2.79 (2H, dt), 2.01 (3H, s), 1.85 (2H, m), 1.7-1.3 (7H, m).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customthe solvent removed by rotary evaporation
  3. customas obtained

Sources & evidence

ORD record
ord-bfdf96cfbbb048eea7222757cac86ed8
Source dataset
uspto-grants-2009_04
Patent number
US07514448B2

Reaction notes

Loading…