2-(2,2-Diphenyl-4-penten-1-yl)-1-azabicyclo[2.2.2]octane → HCID 22759849, compound

HRID 1703814Notes

Reaction equation

HRID 1703814 reaction equation
[C:1]1([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([CH2:17][CH:18]=[CH2:19])[CH2:8][CH:9]2[CH2:14][CH:13]3[CH2:15][CH2:16][N:10]2[CH2:11][CH2:12]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>C(O)C.[Pd]>[C:20]1([C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([CH2:17][CH2:18][CH3:19])[CH2:8][CH:9]2[CH2:14][CH:13]3[CH2:15][CH2:16][N:10]2[CH2:11][CH2:12]3)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 227598642-(2,2-Diphenyl-4-penten-1-yl)-1-azabicyclo[2.2.2]octaneHCID 178418361HCID 178418361, compound

Product 1

HCID 22759849HCID 22759849, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

0.50 Parts of 2-(2,2-diphenyl-4-pentenyl)-1-azabicyclo[2.2.2]octane is dissolved in 50 parts by volume of ethanol. This solution is then added to a Parr hydrogenation bottle which contains 0.05 parts of 5% palladium-on-carbon. The mixture is hydrogenated at room temperature and atmosphere pressure using a 50 ml buret to measure hydrogen uptake. After the hydrogenation is completed the catalyst is removed by filtration. The solution is then stripped in vacuo to afford a gum. Crystallization of this gum from methanol/water affords a white solid which is dried in vacuo at 60° C. for 4 hours to give 2-(2,2-diphenylpentyl)-1-azabicyclo[2.2.2]octane. This compound melts at about 115°-117.5° C. and is represented by the following structural formula ##STR8##

Workup

  1. additionThis solution is then added to a Parr hydrogenation bottle which
  2. customis hydrogenated at room temperature
  3. customis removed by filtration
  4. customto afford a gum
  5. customCrystallization of this gum from methanol/water
  6. customaffords a white solid which
  7. customis dried in vacuo at 60° C. for 4 hours

Sources & evidence

ORD record
ord-e7cb2cd1f83a4d8682f6fc211730b99a
Source dataset
uspto-grants-1978_11
Patent number
US04125531

Reaction notes

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