Hydrochloric Acid → 1-(2-Chloropyridin-4-yl)piperidin-4-one

HRID 451539Notes

Reaction equation

HRID 451539 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:17][CH2:16][C:11]3(OCC[O:12]3)[CH2:10][CH2:9]2)[CH:5]=[CH:4][N:3]=1.Cl.C(=O)([O-])O.[Na+]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:17][CH2:16][C:11](=[O:12])[CH2:10][CH2:9]2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 866567218-(2-Chloropyridin-4-yl)-1,4-dioxa-8-azaspiro[4.5]decane

Product 1

HCID 866567191-(2-Chloropyridin-4-yl)piperidin-4-oneYield 99%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 8-(2-chloropyridin-4-yl)-1,4-dioxa-8-azaspiro[4.5]decane (1.26 g, 4.95 mmol) in acetone (11 mL) was added HCl (2 N, 39.6 mL, 79.1 mmol) and the resulting mixture stirred at 50° C. for 2 hours, then cooled to room temperature. The pH was set to ˜8 by adding solid sodium hydrogen carbonate and then extracted with dichloromethane. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and evaporated to give the title product (1.03 g, 99%) as a white solid.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with dichloromethane
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-f5426199c702457d8b62a4211a4e58cc
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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