Water → HCID 118005821, compound

HRID 2172645Notes

Reaction equation

HRID 2172645 reaction equation
[I-].[CH2:2]([N+:6]1([CH3:15])[CH:14]2[CH:9]([CH2:10][CH2:11][CH2:12][CH2:13]2)[CH2:8][CH2:7]1)[CH2:3][CH2:4][CH3:5].[OH2:16]>>[OH-:16].[CH2:2]([N+:6]1([CH3:15])[CH:14]2[CH:9]([CH2:10][CH2:11][CH2:12][CH2:13]2)[CH2:8][CH2:7]1)[CH2:3][CH2:4][CH3:5]

Participants

3

Reactant 2

HCID 962WaterHCID 118005930HCID 118005930, compound

Product 1

HCID 118005821HCID 118005821, compoundYield 87%

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

  1. additionTo this solution, 70 g of BIO-RAD AG® 1-X8 ion exchange resin was added
  2. filtrationThe solution was filtered

Sources & evidence

ORD record
ord-a274b693f9734d72ab186775f7aa02c7
Source dataset
uspto-grants-2015_06
Patent number
US09056311B2

Reaction notes

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