Sodium Hydroxide → 1-(Pyridin-4-yl)piperidin-4-one

HRID 1840545Notes

Reaction equation

HRID 1840545 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C([O-])(=O)C.[Na+].[OH:17][CH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.[OH-].[Na+]>ClCCl>[N:6]1[CH:11]=[CH:10][C:9]([N:21]2[CH2:22][CH2:23][C:18](=[O:17])[CH2:19][CH2:20]2)=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 79341Piperidin-4-olHCID 517045Sodium AcetateHCID 178418287HCID 178418287, compound

Product 1

HCID 113327931-(Pyridin-4-yl)piperidin-4-oneYield 53.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of pyridinium chlorochromate (24.1 g) and sodium acetate (18.3 g) in dichloromethane (500 ml) was added small portionwise 4-hydroxypiperidine (9.7 g), and the mixture was stirred at room temperature for 5 hours. To the reaction solution was added 1N sodium hydroxide solution, and insoluble materials were dissolved. The separated aqueous layer was extracted with dichloromethane, and combined dichloromethane solution was washed with brine, dried, concentrated and crystallized from toluene to give colorless crystals of 1-(4-pyridyl)-4-piperidinone (9.0 g).

Workup

  1. dissolutionwere dissolved
  2. extractionThe separated aqueous layer was extracted with dichloromethane, and combined dichloromethane solution
  3. washwas washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customcrystallized from toluene

Sources & evidence

ORD record
ord-386ff9a8607f4238af49b5b4fa0577c7
Source dataset
uspto-grants-2004_01
Patent number
US06680312B2

Reaction notes

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