Ethanol → HCID 19907482, compound

HRID 2371541Notes

Reaction equation

[CH2:1]([N:3]([CH2:27][CH3:28])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[CH:12][CH:11]=1)[CH3:2].[CH2:29]([I:31])[CH3:30].[CH2:32](O)[CH3:33]>>[I-:31].[I-:31].[CH2:25]([N+:22]([CH2:29][CH3:30])([CH2:23][CH3:24])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][N+:3]([CH2:32][CH3:33])([CH2:1][CH3:2])[CH2:27][CH3:28])=[CH:15][CH:14]=1)[CH3:26]

Participants

Reactant 3

HCID 702Ethanol

HCID 6340Iodoethane

HCID 19907465HCID 19907465, compound

Product 1

HCID 19907482HCID 19907482, compound

Procedure

First, 300 mg of 1,4-bis(6-diethylaminohexyl)benzene were dissolved in 3 ml of absolute ethanol, and after adding 616 μl of ethyl iodide, the mixture was stirred at a room temperature for 30 minutes, refluxed for 1.5 hours, and then cooled. The mixture was evaporated under a reduced pressure, and after adding 3 ml of acetone, evaporated under a reduced pressure. The residue was dissolved in 1.5 ml of acetone, and the solution was allowed to stand in a freezer for 2 days. The resulting crystal was collected by filtration, washed with ethyl acetate and dried under a reduced pressure to obtain 490 mg of the title compound as a colorless crystal.

Workup

temperaturerefluxed for 1.5 hours
temperaturecooled
customThe mixture was evaporated under a reduced pressure
additionafter adding 3 ml of acetone
customevaporated under a reduced pressure
dissolutionThe residue was dissolved in 1.5 ml of acetone
waitto stand in a freezer for 2 days
filtrationThe resulting crystal was collected by filtration
washwashed with ethyl acetate
customdried under a reduced pressure

Sources & evidence

ORD record: ord-324b6271cd2d4849a9dc23de852e6ee0
Source dataset: uspto-grants-1992_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05093370

Reaction notes

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