N-(3-Chloropropyl)-N,N-dimethyl-1-dodecanaminium bromide → N-(N,N-dimethyl-N-dodecylammonio) propyldiallylmethylammonium Chloride Bromide
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
4
Conditions
- Temperature
- 65 °C
Procedure
A mixture of 22 g diallylmethylamine and 74 g 3-chloropropyldodecyldimethylammonium 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 dialllymethylamine 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 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 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-4b0238b9bdfc4fa7b65e0cabe37fbe38
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07125547B2
Reaction notes
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