Hydrochloric Acid → 1-(Pyridin-4-yl)piperidin-4-one

HRID 2086228Notes

Reaction equation

HRID 2086228 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:16][CH2:15][C:10]3(OCC[O:11]3)[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.Cl>CC(C)=O>[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:16][CH2:15][C:10](=[O:11])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 153824168-(Pyridin-4-yl)-1,4-dioxa-8-azaspiro[4.5]decane

Product 1

HCID 113327931-(Pyridin-4-yl)piperidin-4-oneYield 86.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 8-(4-pyridyl)-1,4-dioxa-8-azaspiro[4.5]decane (172 g) in acetone (700 ml) was combined with 4N hydrochloric acid (700 ml) and stirred at 50° C. for 20 minutes. Acetone was distilled off, and the residue was made alkaline by an addition of an aqueous solution of sodium hydroxide, and then extracted with dichloromethane. After drying and concentrating, the resultant residue was crystallized from ether, collected by filtration and dried to obtain the title compound (119 g) as a pale yellow solid.

Workup

  1. distillationAcetone was distilled off
  2. additionby an addition of an aqueous solution of sodium hydroxide
  3. extractionextracted with dichloromethane
  4. customAfter drying
  5. concentrationconcentrating
  6. customthe resultant residue was crystallized from ether
  7. filtrationcollected by filtration
  8. customdried

Sources & evidence

ORD record
ord-27f8ac3c970846879e41eae6f1fe1785
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

Loading…