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

HRID 345444

Reaction equation

HRID 345444 reaction equation
Cl.Cl[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[OH:9][CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.C(=O)(O)[O-].[Na+]>C(O)CC(C)C>[N:6]1[CH:7]=[CH:8][C:3]([N:13]2[CH2:14][CH2:15][CH:10]([OH:9])[CH2:11][CH2:12]2)=[CH:4][CH:5]=1

Participants

5

Reactant 3

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

Product 1

HCID 234476191-(Pyridin-4-yl)piperidin-4-ol

Reagents, catalysts & solvents 1

HCID 31260Isoamyl AlcoholSolvent

Procedure

A mixture of 4-chloropyridine hydrochloride (7.50 g), 4-hydroxypiperidine (5.06 g) and sodium bicarbonate (10.1 g) in isoamyl alcohol (60 ml) was heated under reflux with stirring for 60 hours and then evaporated. The residue was extracted several times with a boiling mixture of ethyl acetate/methanol (10:1) and the combined extracts were filtered and evaporated. The residue was sublimed at 120°-150° and 0.2 mm pressure to give the pure product, (7.30 g), m.p. 155°-156°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. customevaporated
  4. extractionThe residue was extracted several times
  5. additionwith a boiling mixture of ethyl acetate/methanol (10:1)
  6. filtrationthe combined extracts were filtered
  7. customevaporated
  8. customwas sublimed at 120°-150°
  9. custom0.2 mm pressure to give the pure product, (7.30 g), m.p. 155°-156°

Sources & evidence

ORD record
ord-b02f55d19ab9497a92240296f4862dc8
Source dataset
uspto-grants-1991_10
Patent number
US05057528

Linked notes

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