HCID 22759845, compound → HCID 22759851, compound
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]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
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##