Butyl iodide → HCID 118005930, compound
Reaction equation
[CH3:1][N:2]1[CH:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3]1.[I:11][CH2:12][CH2:13][CH2:14][CH3:15]>CO>[I-:11].[CH2:12]([N+:2]1([CH3:1])[CH:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3]1)[CH2:13][CH2:14][CH3:15]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
20 g (0.14 mmol) of 1-methyl-octahydroindole was mixed with 53 g (0.29 mmol) of 1-iodobutane in 300 mL of methanol. The reaction mixture was heated at reflux for 72 hours. Then, an additional 0.5 mol equivalent of 1-iodobutane was added and the reaction mixture was heated for an additional 12 hours. The reaction mixture was cooled and the solvent removed on a rotary evaporator to give an off-white powder which was used without further purification. The quaternization afforded 39.4 g (86% yield) of 1-butyl-1-methyl-octahydroindolium iodide. The obtained 1-butyl-1-methyl-octahydroindolium iodide (18.15 g) was dissolved in 56 g of deionized water. To this solution, 70 g of BIO-RAD AG® 1-X8 ion exchange resin was added and the slurry was gently stirred at room temperature overnight. The solution was filtered and the filtrate analyzed for hydroxide content by titration of a small aliquot with dilute HCl. The exchange afforded 1-butyl-1-methyl-octahydroindolium hydroxide in 87% yield.
Workup
- temperatureThe reaction mixture was heated
- temperatureat reflux for 72 hours
- temperaturethe reaction mixture was heated for an additional 12 hours
- temperatureThe reaction mixture was cooled
- customthe solvent removed on a rotary evaporator
- customto give an off-white powder which
- customwas used without further purification
Sources & evidence
- ORD record
- ord-114f3333370b4deaaa40eac73003cc06
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09187334B2
Reaction notes
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