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

HRID 1781114Notes

Reaction equation

HRID 1781114 reaction equation
[NH+]12CC[NH+](CC1)C[CH2:2]2.OO.[N:11]12[CH2:18][CH2:17][N+:14]([O-:19])([CH2:15][CH2:16]1)[CH2:13][CH2:12]2.IC.[F:22][B-:23]([F:26])([F:25])[F:24].[Na+]>C1COCC1.C(#N)C>[F:22][B-:23]([F:26])([F:25])[F:24].[CH3:2][O:19][N+:14]12[CH2:17][CH2:18][N:11]([CH2:16][CH2:15]1)[CH2:12][CH2:13]2

Participants

8

Reactant 5

HCID 784Hydrogen PeroxideHCID 6328Methyl iodideHCID 40605551,4-Diazoniabicyclo[2.2.2]octaneHCID 4343483Sodium TetrafluoroborateHCID 111371811,4-Diazabicyclo(2.2.2)octane, 1-oxide

Product 1

HCID 190480541-Methoxy-4-aza-1-azoniabicyclo[2.2.2]octane tetrafluoroborate

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-fluoro-4-methoxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) 1,4-Diazoniabicyclo[2.2.2]octane N-oxide is prepared by the reaction of 1,4-Diazoniabicyclo[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 iodomethane (14.1 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 filtrate is evaporated to afford 1-methoxy-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 filtrate is evaporated

Sources & evidence

ORD record
ord-e78636ac392648f09d0669cfa8fe54aa
Source dataset
uspto-grants-1997_05
Patent number
US05631372

Reaction notes

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