Hydrochloric Acid → HCID 57485529, compound

HRID 749143Notes

Reaction equation

HRID 749143 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]3[CH2:15][CH:12]([CH2:13][CH:14]=2)[CH2:11][N:10](C(OCC)=O)[CH2:9]3)[CH:2]=1.Cl.[OH-].[Na+]>>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]3[CH2:15][CH:12]([CH2:13][CH:14]=2)[CH2:11][NH:10][CH2:9]3)[CH:2]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57485796HCID 57485796, compound

Product 1

HCID 57485529HCID 57485529, compoundYield 15%

Procedure

A mixture of ethyl 6-(3-pyridinyl)-3-azabicyclo[3.3.1]non-6-ene-3-carboxylate (100 mg, 0.370 mmol) and 1.5 mL of concentrated HCl was heated under reflux for 16 h. The mixture was cooled in an ice bath and made basic by adding 5 M aqueous sodium hydroxide. The suspension was extracted with chloroform (3×5 mL), and the extracts were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was filtered though a plug of silica gel, eluting with 90:10:1 dichloromethane/methanol/concentrated ammonium hydroxide, to give the product as an oil (11 mg, 15%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 h
  3. temperatureThe mixture was cooled in an ice bath
  4. extractionThe suspension was extracted with chloroform (3×5 mL)
  5. dry with materialthe extracts were dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. filtrationThe residue was filtered though a plug of silica gel
  9. washeluting with 90:10:1 dichloromethane/methanol/concentrated ammonium hydroxide

Sources & evidence

ORD record
ord-4fa5bba1248b4c08960a5c8f3bb11923
Source dataset
uspto-grants-2008_07
Patent number
US07402592B2

Reaction notes

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