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

HRID 1193401Notes

Reaction equation

HRID 1193401 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.[OH-].[Na+]>Cl>[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 14798Sodium HydroxideHCID 153824168-(Pyridin-4-yl)-1,4-dioxa-8-azaspiro[4.5]decane

Product 1

HCID 113327931-(Pyridin-4-yl)piperidin-4-oneYield 80%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

8-(Pyridin-4-yl)-1,4-dioxa-8-azaspiro[4.5]decane (7.0 g, 31.8 mmol, 1.0 eq.) was dissolved at 0° C. in conc. HCl (42 ml) and stirred for 14 hours at RT. After monitoring by TLC, the reaction solution was rendered alkaline with 2 M NaOH solution and extracted with chloroform (250 ml). The org. phase was dried over sodium sulfate and concentrated under reduced pressure. Yield: 80% (4.5 g, 25.56 mmol)

Workup

  1. extractionextracted with chloroform (250 ml)
  2. dry with materialphase was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-07306fc971974953900836b1d6b3a226
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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