Hydrogen Peroxide → 1-Acetoxy-4-aza-1-azoniabicyclo[2.2.2]octane tetrafluoroborate

HRID 1781116Notes

Reaction equation

HRID 1781116 reaction equation
N12CCN(CC1)CC2.OO.[N:11]12[CH2:18][CH2:17][N+:14]([O-:19])([CH2:15][CH2:16]1)[CH2:13][CH2:12]2.[C:20](Cl)(=[O:22])[CH3:21].[F:24][B-:25]([F:28])([F:27])[F:26].[Na+]>C1COCC1.C(#N)C>[N:11]12[CH2:18][CH2:17][N+:14]([O-:19])([CH2:15][CH2:16]1)[CH2:13][CH2:12]2.[F:24][B-:25]([F:28])([F:27])[F:26].[F:24][B-:25]([F:28])([F:27])[F:26].[C:20]([O:19][N+:14]12[CH2:17][CH2:18][N+:11]([F:24])([CH2:16][CH2:15]1)[CH2:12][CH2:13]2)(=[O:22])[CH3:21].[F:24][B-:25]([F:28])([F:27])[F:26].[C:20]([O:19][N+:14]12[CH2:17][CH2:18][N:11]([CH2:16][CH2:15]1)[CH2:12][CH2:13]2)(=[O:22])[CH3:21]

Participants

9

Reactant 5

HCID 784Hydrogen PeroxideHCID 6367Acetyl chlorideHCID 9237DabcoHCID 4343483Sodium TetrafluoroborateHCID 111371811,4-Diazabicyclo(2.2.2)octane, 1-oxide

Product 2

HCID 190480361-Acetoxy-4-aza-1-azoniabicyclo[2.2.2]octane tetrafluoroborateHCID 867508561-acetoxy-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) 1,4-Diazabicyclo[2.2.2]octane N-oxide

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-acetoxy-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) 1,4-Diazabicyclo[2.2.2]octane N-oxide is prepared by the reaction of 1,4-diazabicyclo[2.2.2]octane with hydrogen peroxide as described by Farkas in J. Chem. Eng. Data (1968) 13,278. 1,4-Diazabicyclo[2.2.2]octane N-oxide (12.8 g, 10 mmol) in THF (100 mL) is reacted with acetyl chloride (7.9 g, 10 mmol) until the reaction is complete by TLC. The reaction is evaporated, diluted with acetonitrile (100 mL) and sodium tetrafluoroborate (40 g, 20 mmol) added. The solution is stirred overnight at room temperature and then filtered to remove all undissolved salts. The flltrate is evaporated to afford 1-acetoxy-4-aza-1-azoniabicyclo[2.2.2]octane tetrafluoroborate.

Workup

  1. customThe reaction is evaporated
  2. additionadded
  3. filtrationfiltered
  4. customto remove all undissolved salts
  5. customThe flltrate is evaporated

Sources & evidence

ORD record
ord-f9e0c9f2c0c944d59a70ae8393a741c1
Source dataset
uspto-grants-1997_05
Patent number
US05631372

Reaction notes

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