N-Methylpiperidine → 1-Methyl-3-propyl piperidinium propyl sulfate

HRID 1821108Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH2:8]([O:11][S:12](=[O:18])(=[O:17])[O:13][CH2:14][CH2:15][CH3:16])[CH2:9][CH3:10]>C1(C)C=CC=CC=1>[CH2:8]([O:11][S:12]([O-:18])(=[O:17])=[O:13])[CH2:9][CH3:10].[CH3:1][NH+:2]1[CH2:7][CH2:6][CH2:5][CH:4]([CH2:14][CH2:15][CH3:16])[CH2:3]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a 50 ml four necked flask equipped with a stirrer, a dropping funnel, a cooling tube and a thermometer, 4.96 g (0.05 mol) of 1-methyl piperidine and 5 ml of toluene were charged, after heating to 50° C., 10.02 g (0.055 mol) of dipropyl sulfuric acid was dropped slowly taking one hour or more. After reacting for 10 hours, 13.37 g of 1-methyl-3-propyl piperidinium propyl sulfate was obtained by drying under a reduced pressure. Then, 13.37 g of the obtained 1-methyl-3-propyl piperidinium propyl sulfate was dissolved in 8 ml of water, and a solution in which 10.5 g of potassium bis(fluorosulfonyl)imide was dissolved in 8 ml of water was added thereto at a room temperature and stirred. From separated two layers, the lower layer was fractionated and by-products were removed by adding 40 wt % of purified water and water washing five times, and vacuum drying was applied to obtain 15.31 g of 1-methyl-3-propyl pyrrolinium bis(fluorosulfonyl) imide. As a result of ICP analysis, the total alkali metals was 1.8 ppm, chloride ion was 0.5 ppm, and each of iodide and bromide ions was 0.1 ppm or less (lower than ICP detection limit).

Workup

waittaking one hour or more

Sources & evidence

ORD record: ord-ec81efdcf14f48acbec3bde5431e329b
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07605271B2

Reaction notes

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