HCID 22759845, compound → HCID 22759851, compound

HRID 597227Notes

Reaction equation

HRID 597227 reaction equation
[C:1]1([C:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:8][CH:9]2[C:14](=[O:15])[CH:13]3[CH2:16][CH2:17][N:10]2[CH2:11][CH2:12]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)C.[Pd]>[C:18]1([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][CH:9]2[C:14](=[O:15])[CH:13]3[CH2:16][CH2:17][N:10]2[CH2:11][CH2:12]3)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 1

HCID 22759845HCID 22759845, compound

Product 1

HCID 22759851HCID 22759851, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

18.9 Parts of a mixture of the two isomers (cis and trans) of 2-(2,2-diphenylethylidenyl)-1-azabicyclo[2.2.2]-octan -3-one, and 2-(2,2-diphenylethenyl)-1-azabicyclo[2.2.2]-octan-3-one is dissolved in approximately 790 parts ethanol. Then, 4 parts of a 5% palladium-on-carbon catalyst is added and the mixture shaken in a Parr Shaker at room temperature and a pressure of 36-60 psi for 3 hours. The catalyst is removed by filtration and the solvents removed in vacuo. The residual white solid is dissolved in 560 parts of hot n-pentane. The solution is filtered and then concentrated on a steam bath to a volume of about 190 ml. Standing at room temperature affords a precipitate which is filtered, washed with n-pentane and dried in vacuo to provide a white solid. This solid is recrystallized from ethyl ether to afford 2-(2,2-diphenylethyl)-1-azabicyclo[2.2.2]octan-3-one. This compound begins to shrink at 103° C., clouds at 104°-105° C. and melts at about 107° C. and is represented by the following structural formula. ##STR9##

Workup

  1. customThe catalyst is removed by filtration
  2. customthe solvents removed in vacuo
  3. dissolutionThe residual white solid is dissolved in 560 parts of hot n-pentane
  4. filtrationThe solution is filtered
  5. concentrationconcentrated on a steam bath to a volume of about 190 ml
  6. customStanding at room temperature
  7. customaffords a precipitate which
  8. filtrationis filtered
  9. washwashed with n-pentane
  10. customdried in vacuo
  11. customto provide a white solid
  12. customThis solid is recrystallized from ethyl ether

Sources & evidence

ORD record
ord-7a1f44cafbd344eca557cbd23fc4b562
Source dataset
uspto-grants-1977_03
Patent number
US04013667

Reaction notes

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