Dabco → 1,4-Diazabicyclo[2.2.2]octane, hydrochloride

HRID 429700Notes

Reaction equation

HRID 429700 reaction equation
[CH2:1]1[N:6]2[CH2:7][CH2:8][N:3]([CH2:4][CH2:5]2)[CH2:2]1.[Cl-:9].[Li+]>O1CCCC1>[CH2:1]1[N:6]2[CH2:7][CH2:8][N:3]([CH2:4][CH2:5]2)[CH2:2]1.[ClH:9]

Participants

4

Reactant 2

HCID 9237DabcoHCID 433294Lithium Chloride

Product 1

HCID 5198321,4-Diazabicyclo[2.2.2]octane, hydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 100 ml of anhydrous tetrahydrofurane under argon at 0° C., 20.27 g (10 mmoles) of 4-styrenesulfonyl chloride CH2═CHC6H4SO2Cl (commercially available from Monomer-Polymer & Dajac Laboratories) were reacted with 14.91 g (10 mmoles) of trifluoromethane-sulfonamide CF3SO2NH2 and 22.44 g (20 mmoles) of (DABCO). After 2 hours at 0° C. and 48 hours at room temperature, the solution was filtered to remove the DABCO hydrochloride formed, and it was thereafter treated with 424 mg (10 mmoles) of anhydrous lithium chloride, which is stored and weighed in a glove box. Immediately, a precipitate of DABCO hydrochloride was formed and the reaction mixture was then again filtered after stirring for 6 hours. After evaporation and drying under vacuum, during 24 hours at room temperature, 31.16 g of the lithium salt of trifluoromethane-sulfonyl(4-styrenesulfonyl)imide were recovered which have a purity characterized by a proton and fluorine RMN higher than 97%.

Workup

  1. filtration48 hours at room temperature, the solution was filtered
  2. customto remove the DABCO hydrochloride
  3. customformed
  4. customweighed in a glove box

Sources & evidence

ORD record
ord-0e08a2ac4388443381e903b2726cba2d
Source dataset
uspto-grants-2001_11
Patent number
US06319428B1

Reaction notes

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