Reaction #1552034

Reaction equation

N,N-dimethylazonanium iodide

water

hydroxide

→

N,N-dimethylazonanium hydroxide

Conditions

Workup

1. 1
   OtherThe product was further purified
2. 2
   workup.DISSOLUTIONby dissolving in a minimal amount of isopropyl alcohol
3. 3
   Otherprecipitating the product out
4. 4
   workup.ADDITIONby adding diethyl ether
5. 5
   FiltrationThe precipitate was filtered
6. 6
   Otherdried on a rotary evaporator in a hot bath (70° C.) at reduced pressure
7. 7
   Otherto give the desired pure product in about 93% yield
8. 8
   workup.ADDITIONwas added
9. 9
   workup.WAITThe resulting slurry was left
10. 10
    FiltrationThe slurry was filtered

Procedure

A 3-neck round-bottom flask (equipped with a mechanical stirrer, a heating mantle and reflux condenser) was charged with a one molar equivalent of azonane in enough methanol to make a 0.5M concentration solution with respect to azonane. To this solution, 1.5 molar equivalent of potassium bicarbonate was added. The solution was stirred for several minutes and then 2.5 molar equivalent of methyl iodide was added dropwise via an addition funnel. Once the addition of methyl iodide was completed, the reaction mixture was heated at reflux (about 55° C.) for several hours. The heat source was turned off and the reaction mixture was then stirred at room temperature for additional 48 hours. The progress of the reaction was monitored by NMR. Once completed, the reaction mixture was transferred to a recovery flask and the solvent removed on a rotary evaporator at reduced pressure. The obtained solids, a mixture of the product and potassium bicarbonate, were suspended in chloroform (500 mL CHCl3/l mol azonane). The resulting two-phase solution was filtered through a fritted-glass funnel. The filtrate containing the product (N,N-dimethylazonanium iodide) was concentrated on a rotary evaporator at reduced pressure to give the desired salt as an off-white solid. The product was further purified by dissolving in a minimal amount of isopropyl alcohol and precipitating the product out by adding diethyl ether. The precipitate was filtered and dried on a rotary evaporator in a hot bath (70° C.) at reduced pressure to give the desired pure product in about 93% yield. The obtained N,N-dimethylazonanium iodide was dissolved in deionized water (1 mL H2O/1 mmol salt) and then 1.1 g of hydroxide-based ion exchange resin/1 mmol salt was added. The resulting slurry was left to stir gently for a few hours. The slurry was filtered and the filtrate was analyzed by titration of a small aliquot with dilute HCl. The exchange afforded N,N-dimethylazonanium hydroxide in nearly quantitative yield.

Source