Piperidin-4-ol → 1-(Pyridin-4-yl)piperidin-4-ol

HRID 2186132Notes

Reaction equation

HRID 2186132 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Cl.Cl[C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1.C(=O)([O-])O.[Na+]>C(O)CC(C)C>[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 79341Piperidin-4-olHCID 818524-Chloropyridine hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 234476191-(Pyridin-4-yl)piperidin-4-olYield 34.1%

Reagents, catalysts & solvents 1

HCID 31260Isoamyl AlcoholSolvent

Procedure

A mixture of 4-hydroxypiperidine (30 g), 4-chloropyridine hydrochloride (45 g), sodium hydrogen carbonate (60 g) and isoamylalcohol (300 ml) was refluxed for 60 hours. The reaction solution was cooled, and insoluble materials were filtered off. The filtrate was concentrated, and the resulting crystals were washed with ether and dried to give 4-hydroxy-1-(4-pyridyl)piperidine (18 g).

Workup

  1. temperaturewas refluxed for 60 hours
  2. temperatureThe reaction solution was cooled
  3. filtrationinsoluble materials were filtered off
  4. concentrationThe filtrate was concentrated
  5. washthe resulting crystals were washed with ether
  6. customdried

Sources & evidence

ORD record
ord-01f2441f2e59492485cd96fab58fe907
Source dataset
uspto-grants-2002_06
Patent number
US06403595B1

Reaction notes

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