Diethyl Ether → HCID 10176282, compound

HRID 396275Notes

Reaction equation

HRID 396275 reaction equation
[CH:1]12[CH2:9][CH:5]([CH2:6][CH2:7][CH2:8]1)[CH2:4][CH2:3][NH:2]2.[CH2:10](Br)[CH:11]=[CH2:12].C(=O)([O-])[O-].[K+].[K+].CCOCC>C(COC)OC>[CH2:12]([N:2]1[CH2:3][CH2:4][CH:5]2[CH2:9][CH:1]1[CH2:8][CH2:7][CH2:6]2)[CH:11]=[CH2:10]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 123129732-Azabicyclo(3.3.1)nonane

Product 1

HCID 10176282HCID 10176282, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution (6.5 ml) of 2-azabicyclo[3.3.1]nonane (100 mg, 0.62 mmol) in dimethoxyethane were added allylbromide (105 mg, 0.87 mmol) and potassium carbonate (94 mg, 0.68 mmol) and the mixture was heated at reflux temperature for 3.5 hours. Ether (10 ml) was added to the reaction mixture, followed by filtration and removal of the solvent, and the residue was purified with silica gel column chromatography (chloroform-methanol-triethylamine=100:9:1), to obtain 2-allyl-2-azabicyclo[3.3.1]nonane (52 mg, 51%) as a colorless oily substance.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 3.5 hours
  3. filtrationfollowed by filtration and removal of the solvent
  4. customthe residue was purified with silica gel column chromatography (chloroform-methanol-triethylamine=100:9:1)

Sources & evidence

ORD record
ord-97b3765897aa46a992ca8ee18129f1c8
Source dataset
uspto-grants-2003_08
Patent number
US06608080B1

Reaction notes

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