Sodium Hydroxide → HCID 22599566, compound

HRID 1760116Notes

Reaction equation

HRID 1760116 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][C:10](=[O:13])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N-:14]=[N+]=[N-].[Na+].[OH-].[Na+]>C(O)(=O)C.S(=O)(=O)(O)O>[C:1]1([N:7]2[CH:12]=[CH:11][NH:14][C:10](=[O:13])[CH:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 33557Sodium AzideHCID 4130091-Phenyl-4-piperidinone

Product 1

HCID 22599566HCID 22599566, compoundYield 92.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent

Procedure

To the product from Step A (12.54 g, 71.56 mmols) in glacial acetic acid (60 mL) and concentrated sulfuric acid (30 mL) at 0° C. was added sodium azide (5.12 g, 78.7 mmols) in five portions of 1.024 g over a period of 4 hours. The resultant pale yellow mixture was allowed to warm to room temperature with stirring under nitrogen for 17 hours. The mixture was poured onto ice and neutralized to pH 7 with 5 M aq. NaOH. The product was extracted into methylene chloride (2×400 mL) and the combined organic extracts were dried over sodium sulfate, filtered, and concentrated to a pale yellow solid. Flash chromatography purification eluting with EtOAc gradient to EtOAc/MeOH (95:5) yielded 12.37 g (91%) of the title intermediate as a pale yellow solid.

Workup

  1. extractionThe product was extracted into methylene chloride (2×400 mL)
  2. dry with materialthe combined organic extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to a pale yellow solid
  5. customFlash chromatography purification
  6. washeluting with EtOAc gradient to EtOAc/MeOH (95:5)

Sources & evidence

ORD record
ord-4f6ae2b5440b416ea2f1ed49fa692ddd
Source dataset
uspto-grants-2005_01
Patent number
US06838455B2

Reaction notes

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