Ethanol → HCID 19911836, compound
Reaction equation
[O:1](C)[S:2]([C:5]([F:8])([F:7])[F:6])(=[O:4])=[O:3].CC1CN2CCN1CC2.C(O)C.[O-:22][S:23]([C:26]([F:29])([F:28])[F:27])(=[O:25])=[O:24].[O-]S(C(F)(F)F)(=O)=O.[CH3:38][N+:39]12[CH2:46][CH2:45][N+:42]([CH3:47])([CH2:43][CH2:44]1)[CH2:41][CH:40]2C>C(#N)C>[O-:4][S:2]([C:5]([F:8])([F:7])[F:6])(=[O:3])=[O:1].[CH3:38][N+:39]12[CH2:46][CH2:45][N+:42]([CH3:47])([CH2:43][CH2:44]1)[CH2:41][CH2:40]2.[O-:25][S:23]([C:26]([F:29])([F:28])[F:27])(=[O:24])=[O:22]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Methyl triflate (3.2 g, 19.5 mmol) was added dropwise to a cold (0 ° C) stirred solution of 2-methyl-1,4-diazabicyclo [2,2,2]octane (2.5 g, 20.0 mmol) in dry acetonitrile under an atmosphere of dry nitrogen. The mixture was stirred at 0° C. for 1 hour and then at 20° C. overnight. The orange solution obtained was treated dropwise with ethanol until precipitation of a white solid ceased; this solid was recovered by filtration, washed with ethanol, dried in vacuo at room temperature and shown by n.m.r. spectroscopy (1H and 19F) to be 1,2,4-trimethyl-1,4-diazoniabicyclo[2,2,2]octane ditriflate (0.45 g, 0.99 mmol, 5%). Removal of acetonitrile from the filtrate in vacuo left an orange oil (3.6 g, 12.4 mmol, 64%), shown by n.m.r. spectroscopy (1H and 19F) to be methyl-N-methyl-1,4-diazabicyclo [2,2,2]octane triflate.
Workup
- customat 20° C.
- customovernight
- customThe orange solution obtained
- filtrationthis solid was recovered by filtration
- washwashed with ethanol
- customdried in vacuo at room temperature
- customRemoval of acetonitrile from the filtrate in vacuo
Sources & evidence
- ORD record
- ord-0bb60c50c2e146f6993c962ff66f25ca
- Source dataset
- uspto-grants-1992_02
- Patent number
- US05086178
Reaction notes
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