Hydrochloric Acid → HCID 70471430, compound

HRID 745544Notes

Reaction equation

HRID 745544 reaction equation
[ClH:1].[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]=[C:13]2[CH:18]3[CH2:19][CH2:20][N:15]([CH2:16][CH2:17]3)[CH2:14]2)=[CH:7][CH:6]=1)([O-])=O.[Sn].Cl.[OH-].[Na+]>O>[ClH:1].[ClH:1].[NH2:2][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]=[C:13]2[CH:18]3[CH2:17][CH2:16][N:15]([CH2:20][CH2:19]3)[CH2:14]2)=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5352426Tin atomHCID 70471396HCID 70471396, compound

Product 1

HCID 70471430HCID 70471430, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 7.75 g (0.03 mole) of 3-[2-(4-nitrophenyl)ethylidene]-1-azabicyclo[2.2.2]octane hydrochloride and 7.12 g (0.06 mole) of mossy tin suspended in 50 ml of water add 30 ml (0.36 mole) of concentrated hydrochloric acid in six portions with good mixing. Maintain the reaction just near the boiling point, cooling if necessary. After the reaction slows heat the mixture at 80°-90° C. with good stirring for 1 hour. Follow the progress of the reaction by thin-layer chromatography on silica gel (acetonitrile:ammonium hydroxide, 95:5). At the completion of the reaction cool the mixture to 0°-5° C. Add 20% sodium hydroxide to bring the mixture to pH>12. Filter any solids if necessary and wash the solids well with methylene chloride solution. Extract the aqueous mixture with four 100 ml portions of methylene chloride. Combine the methylene chloride washes and extracts, and wash them with 50 ml of water and 50 ml of saturated sodium chloride solution. Dry the methylene chloride solution over anhydrous sodium sulfate, filter and remove the solvent in vacuo to provide the title compound as the free base.

Workup

  1. temperatureMaintain
  2. customthe reaction just near the boiling point
  3. temperaturecooling if necessary
  4. temperatureAfter the reaction slows heat the mixture at 80°-90° C.
  5. customthe progress of the reaction by thin-layer chromatography on silica gel (acetonitrile:ammonium hydroxide, 95:5)
  6. temperatureAt the completion of the reaction cool the mixture to 0°-5° C
  7. filtrationFilter any solids if necessary and
  8. washwash the solids well with methylene chloride solution
  9. extractionExtract the aqueous mixture with four 100 ml portions of methylene chloride
  10. washwash them with 50 ml of water and 50 ml of saturated sodium chloride solution
  11. dry with materialDry the methylene chloride solution over anhydrous sodium sulfate
  12. filtrationfilter
  13. customremove the solvent in vacuo

Sources & evidence

ORD record
ord-6dee3211401d416e9dfd7526b6ea88bb
Source dataset
uspto-grants-1986_07
Patent number
US04599344

Reaction notes

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