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.C(OCC)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

Procedure

25.7 Parts of a mixture of the 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 1000 parts by volume of ethanol. Then 5 parts of 5% palladium-on-carbon is added and the mixture is hydrogenated using a Parr low-pressure hydrogenator, at room temperature and a pressure of 60-30 psi for 4 hours. After the hydrogenation is completed the catalyst is removed by filtration. The solution is then stripped in vacuum to give a solid. The solid is dissolved in 500 parts by volume of hot ethyl ether. The solution is filtered and then concentrated on a steam bath to a volume of about 150 parts by volume. The concentrated solution is cooled in an ice-bath to afford a precipitate which is filtered off from the solvent, washed with cold ethyl ether 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 melting at 103°-107° C. This compound is represented by the following structural formula ##STR3##