Propane sultone → HCID 131714780, compound

HRID 745542Notes

Reaction equation

HRID 745542 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]=[C:10]2[CH:15]3[CH2:16][CH2:17][N:12]([CH2:13][CH2:14]3)[CH2:11]2)=[CH:4][CH:3]=1.[CH2:18]1[CH2:24][S:21](=[O:23])(=[O:22])[O:20][CH2:19]1>C(O)C>[OH-:20].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]=[C:10]2[CH:15]3[CH2:14][CH2:13][N+:12]([CH2:19][CH2:18][CH2:24][S:21]([OH:23])(=[O:22])=[O:20])([CH2:17][CH2:16]3)[CH2:11]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14264Propane sultoneHCID 54118471HCID 54118471, compound

Product 1

HCID 131714780HCID 131714780, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
-10 °C

Procedure

Combine 7.43 g (0.03 mole) of 3-[2-(4-chlorophenyl)ethylidene]-1-azabicyclo[2.2.2]octane and 5.49 g (0.045 mole) of 1,3-propanesultone in 30 ml of ethanol and heat at reflux for 1-2 hours. Follow the reaction by thin-layer chromatography on silica gel (acetonitrile:NH4OH, 90:10). At the completion of the reaction cool the mixture to -10° C. Collect the resulting solid by filtration and wash with cold ethanol to provide the title compound.

Workup

  1. temperatureat reflux for 1-2 hours
  2. customthe reaction by thin-layer chromatography on silica gel (acetonitrile:NH4OH, 90:10)
  3. customCollect the resulting solid
  4. filtrationby filtration
  5. washwash with cold ethanol

Sources & evidence

ORD record
ord-4d33fde7e230477c9617a1934c85eb62
Source dataset
uspto-grants-1986_07
Patent number
US04599344

Reaction notes

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