Sodium Hydroxide → 1-Phenyl-4-piperidinone

HRID 1068499Notes

Reaction equation

HRID 1068499 reaction equation
[C:1]1([N:7]2[CH2:16][CH2:15][C:10]3(OCC[O:11]3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C(O)(=O)C.O.Cl>[C:1]1([N:7]2[CH2:8][CH2:9][C:10](=[O:11])[CH2:15][CH2:16]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 114700398-Phenyl-1,4-dioxa-8-azaspiro[4.5]decane

Product 1

HCID 4130091-Phenyl-4-piperidinone

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

8-Phenyl-1,4-dioxa-8-azaspiro[4.5]decane (18.1 g, 82.5 mmol) was dissolved in a mixture of acetic acid (150 mL), water (150 mL), and conc. hydrochloric acid (38 mL) and the resulting solution was heated to 50° C. for 18 hrs. The reaction mixture was cooled in an ice-water bath, and sodium hydroxide pellets were added in portions until the mixture was neutralized. This mixture was extracted with dichloromethane (3×300 mL) and the combined organic extracts were dried over MgSO4, filtered, and concentrated in vacuo to give a dark oil. Chromatography on silica gel, eluting with hexane—10% ethyl acetate gave the product as a pale yellow oil.

Workup

  1. temperatureThe reaction mixture was cooled in an ice-water bath
  2. extractionThis mixture was extracted with dichloromethane (3×300 mL)
  3. dry with materialthe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a dark oil
  7. washChromatography on silica gel, eluting with hexane—10% ethyl acetate

Sources & evidence

ORD record
ord-ab2380bd7d8f4947ad00b02859ec558b
Source dataset
uspto-grants-2001_06
Patent number
US06248756B1

Reaction notes

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