N-(3-Chloropropyl)-N,N-dimethyl-1-dodecanaminium bromide → N-(N,N-dimethyl-N-dodecylammonio) propyldiallylmethylammonium Chloride Bromide

HRID 2086512Notes

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

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 22 g of diallylmethylamine and 74 g 3-chloropropyldodecyldimethylammonium bromide was dissolved in 100 mL of methanol and the reaction mixture was stirred at 65° C. for 48 hours. After cooling to room temperature, the solvent was removed under reduced pressure. The residual viscous oil was precipitated into 800 mL of ether with rapid stirring. The ether layer was decanted and the residue was again treated with 500 mL of 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 70 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 of ether with rapid stirring
customThe ether layer was decanted
additionthe residue was again treated with 500 mL of 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-8e4d5a09f0d44201bbf6d5c50f8d738b
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06726905B1

Reaction notes

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