4-Pyridineethanol → 4-Piperidineethanol

HRID 1791636Notes

Reaction equation

HRID 1791636 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1>C(O)(=O)C.[Pt]=O>[NH:7]1[CH2:8][CH2:9][CH:4]([CH2:3][CH2:2][OH:1])[CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 729214-Pyridineethanol

Product 1

HCID 739534-PiperidineethanolYield 46%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 4-(2-hydroxyethyl)pyridine (1.8 g, 14.6 mol) in acetic acid (15 ml) containing platinum oxide (200 mg) was hydrogenated for 20 hours at 3.3–4 atmospheres pressure. After filtration, the filtrate was evaporated and azeotroped twice with toluene. The residue was triturated with 2N sodium hydroxide and solid sodium hydroxide was added to adjust the pH to 13. The volatiles were removed under vacuum and the residue was triturated with ether, filtered, washed with methylene chloride, and dried under vacuum to give 2-(piperidin-4-yl)-1-ethanol (860 mg, 46%).

Workup

  1. filtrationAfter filtration
  2. customthe filtrate was evaporated
  3. customazeotroped twice with toluene
  4. customThe residue was triturated with 2N sodium hydroxide and solid sodium hydroxide
  5. additionwas added
  6. customThe volatiles were removed under vacuum
  7. customthe residue was triturated with ether
  8. filtrationfiltered
  9. washwashed with methylene chloride
  10. customdried under vacuum

Sources & evidence

ORD record
ord-96881d55c9224543ab8da979c8651f3b
Source dataset
uspto-grants-2006_07
Patent number
US07074800B1

Reaction notes

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