Hepta-1,6-dien-4-amine → N-(N,N-Dimethyl-N-dodecylammonio)butyldiallylmethylammonium Chloride Bromide

HRID 397227

Reaction equation

[CH2:1]([CH:4]([NH2:8])[CH2:5][CH:6]=[CH2:7])[CH:2]=[CH2:3].[Br-:9].[Cl:10][CH2:11][CH2:12][CH2:13][CH2:14][N+:15]([CH3:29])([CH3:28])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>CO>[Br-:9].[Cl-:10].[CH3:28][N+:15]([CH2:14][CH2:13][CH2:12][CH2:11][NH2+:8][CH:4]([CH2:5][CH:6]=[CH2:7])[CH2:1][CH:2]=[CH2:3])([CH3:29])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 22 g diallylmethylamine and 75 g 4-chlorobutyldimethyldodecyl-ammonium bromide were dissolved in 100 mL methanol and the reaction mixture was stirred at 65° C. for 48 hours. The progress of the reaction was monitored by the disappearance of the diallylmethylamine by thin layer chromatography (TLC). After cooling to room temperature, the solvent was removed under reduced pressure. The residual viscous oil was precipitated into 800 mL dry ether with rapid stirring. The ether layer was decanted and the residue was again treated with 500 mL dry ether. After stirring for 15 minutes the solvent was removed and the oily residue was dried under vacuum at 35° C. for 48 hours, yielding 65 g of the product.

Workup

temperatureAfter cooling to room temperature
customthe solvent was removed under reduced pressure
customThe residual viscous oil was precipitated into 800 mL dry ether with rapid stirring
customThe ether layer was decanted
additionthe residue was again treated with 500 mL dry ether
stirringAfter stirring for 15 minutes the solvent
customwas removed
customthe oily residue was dried under vacuum at 35° C. for 48 hours

Sources & evidence

ORD record: ord-ca68ff58234a4e23b8c52b21d7ba058e
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06610283B1

Linked notes

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