1-Bromodecane → N-decyldiallylmethylammonium bromide

HRID 397225Notes

Reaction equation

HRID 397225 reaction equation
[CH2:1]([CH:4]([NH2:8])[CH2:5][CH:6]=[CH2:7])[CH:2]=[CH2:3].[Br:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>CO>[Br-:9].[CH2:10]([NH2+:8][CH:4]([CH2:5][CH:6]=[CH2:7])[CH2:1][CH:2]=[CH2:3])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 81731-BromodecaneHCID 12791689Hepta-1,6-dien-4-amine

Product 1

HCID 86593799N-decyldiallylmethylammonium bromideYield 78.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

Diallylmethylamine (33.3 g) and 1-bromodecane (66.6 g) were dissolved in 100 mL methanol and the reaction mixture was stirred at 65° C. for 48 hours. After cooling to room temperature, the methanol 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 78 g of the product.

Workup

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

Sources & evidence

ORD record
ord-35b01ac8e112445baf5f9e67d8c6995b
Source dataset
uspto-grants-2003_08
Patent number
US06610283B1

Reaction notes

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