Allyl bromide → 2-(2,2-Diphenyl-4-penten-1-yl)-1-azabicyclo[2.2.2]octane

HRID 1703813Notes

Reaction equation

HRID 1703813 reaction equation
[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[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.[CH2:23]1[CH2:28]CCC[CH2:24]1.C([Li])CCC.BrCC=C>CCCCCC>[C:17]1([C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([CH2:28][CH:23]=[CH2:24])[CH2:8][CH:9]2[CH2:14][CH:13]3[CH2:15][CH2:16][N:10]2[CH2:11][CH2:12]3)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 8078CyclohexaneHCID 20339673HCID 20339673, compoundHCID 178418339Butyllithium

Product 1

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

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a solution of 2.91 parts of 2-(2,2-diphenylethyl)-1-azabicyclo[2.2.2]octane in 40 parts by volume of cyclohexane are added under a nitrogen atmosphere 4.6 parts by volume of a 2.5 M solution of butyl lithium in hexane and 1.5 parts by volume of N,N,N'N'-tetramethylethylenediamine. The mixture is heated to reflux, with stirring, for 12/3 hour and then cooled to room temperature. 1.45 Parts of 3-bromopropene is then added during a 5-second period. Stirring is continued for about 6 minutes during which time the internal temperature reaches a maximum of 43° C. and then subsides. The resulting yellow mixture is washed with seven portions of water and then extracted with dilute hydrochloride acid. The acidic, aqueous extract is washed with ethyl ether and then basefied with aqueous sodium hydroxide resulting in the liberation of an oil. This oil is then extracted with ethyl ether. The ethereal extract is dried over anhydrous sodium sulfate and stripped in vacuo to give a light brown oil. This oil is crystallized from methanol and water to afford as a white solid, 2-(2,2-diphenyl-4-pentenyl)-1-azabicyclo[2.2.2]octane melting at about 95.5°-98° C. This compound is represented by the following structural formula: ##STR7##

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux
  3. stirringStirring
  4. waitis continued for about 6 minutes during which time
  5. customa maximum of 43° C.
  6. washThe resulting yellow mixture is washed with seven portions of water
  7. extractionextracted with dilute hydrochloride acid
  8. extractionThe acidic, aqueous extract
  9. washis washed with ethyl ether
  10. extractionThis oil is then extracted with ethyl ether
  11. extractionThe ethereal extract
  12. dry with materialis dried over anhydrous sodium sulfate
  13. customto give a light brown oil
  14. customThis oil is crystallized from methanol and water

Sources & evidence

ORD record
ord-b96161e91b5d4dbc94814b4c4d21212f
Source dataset
uspto-grants-1978_11
Patent number
US04125531

Reaction notes

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