Hydrochloric Acid → 1-(4-Chlorophenyl)-2-[(3-oxo-1-azabicyclo[2.2.2]oct-2-yl)methyl]-1,3-butanedione hydrochloride

HRID 745555

Reaction equation

HRID 745555 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[CH2:9][C:10](=[O:12])[CH3:11])=[CH:4][CH:3]=1.[CH2:14]=[C:15]1[C:20](=[O:21])[CH:19]2[CH2:22][CH2:23][N:16]1[CH2:17][CH2:18]2.Cl>CC(C)=O>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:13])[CH:9]([CH2:14][CH:15]2[C:20](=[O:21])[CH:19]3[CH2:22][CH2:23][N:16]2[CH2:17][CH2:18]3)[C:10](=[O:12])[CH3:11])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2380831-(4-Chlorophenyl)butane-1,3-dioneHCID 3229732-Methylene-3-quinuclidone

Product 1

HCID 139715381-(4-Chlorophenyl)-2-[(3-oxo-1-azabicyclo[2.2.2]oct-2-yl)methyl]-1,3-butanedione hydrochloride

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 93.10 g (0.47 mole) 1-(4-chlorophenyl)-1,3-butanedione in 500 ml acetone add 60.0 g (0.39 mole) 2-methylene-3-quinuclidinone. Stir the solution at reflux for about 24 hours. Follow the progress of the reaction by thin-layer chromatography on silica gel (EtOAc:MeOH, 9:1). At the completion of the reaction, chill the solution in an ice/water bath. Acidify dropwise with 35 ml concentrated hydrochloric acid to precipitate the product. Collect the precipitate by filtration to obtain the title compound as a mixture of diastereomers.

Workup

  1. temperatureat reflux for about 24 hours
  2. customthe progress of the reaction by thin-layer chromatography on silica gel (EtOAc:MeOH, 9:1)
  3. customAt the completion of the reaction
  4. temperaturechill the solution in an ice/water bath
  5. customto precipitate the product
  6. customCollect the precipitate
  7. filtrationby filtration

Sources & evidence

ORD record
ord-e708001b140e4ae7a59fe77869336848
Source dataset
uspto-grants-1986_07
Patent number
US04599344

Linked notes

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