HCID 22759845, compound → HCID 22759851, compound

HRID 1703811Notes

Reaction equation

HRID 1703811 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

5

Reactant 1

HCID 22759845HCID 22759845, compound

Product 1

HCID 22759851HCID 22759851, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

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##

Workup

  1. customis removed by filtration
  2. customto give a solid
  3. filtrationThe solution is filtered
  4. concentrationconcentrated on a steam bath to a volume of about 150 parts by volume
  5. temperatureThe concentrated solution is cooled in an ice-bath
  6. customto afford a precipitate which
  7. filtrationis filtered off from the solvent
  8. washwashed with cold ethyl ether
  9. customdried in vacuo
  10. customto provide a white solid
  11. customThis solid is recrystallized from ethyl ether

Sources & evidence

ORD record
ord-25bc491189d0489d91a3abf9cb36524a
Source dataset
uspto-grants-1978_11
Patent number
US04125531

Reaction notes

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