Methanol → 1,6-Bis(diallylmethylammonio)hexane Dibromide

HRID 397222Notes

Reaction equation

HRID 397222 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]Br.CO>C(OCC)C>[Br-:9].[Br-:9].[CH2:1]([CH:4]([NH2+:8][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][NH2+:8][CH:4]([CH2:5][CH:6]=[CH2:7])[CH2:1][CH:2]=[CH2:3])[CH2:5][CH:6]=[CH2:7])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 123681,6-DibromohexaneHCID 12791689Hepta-1,6-dien-4-amine

Product 1

HCID 219098621,6-Bis(diallylmethylammonio)hexane DibromideYield 184.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
65 °C

Procedure

To a 1 L Morton flask was added diallylmethylamine (74.6 g), 1,6-dibromohexane (77 g), and methanol (100 mL). The mixture was heated to 65° C. for 17 h, and then allowed to cool to room temperature. Diethylether (300 mL) was added and the mixture was stirred for 1 hr. The solid was collected by filtration and resuspended in diethylether (200 mL). The mixture was stirred for 1 hr, and the solid again collected by filtration. The solid was then dried in a vacuum oven at 50° C. for 3 days to yield 136 g of product.

Workup

  1. temperatureto cool to room temperature
  2. filtrationThe solid was collected by filtration
  3. stirringThe mixture was stirred for 1 hr
  4. filtrationthe solid again collected by filtration
  5. customThe solid was then dried in a vacuum oven at 50° C. for 3 days

Sources & evidence

ORD record
ord-79a8d294cf52452b9eaf5d2474b41725
Source dataset
uspto-grants-2003_08
Patent number
US06610283B1

Reaction notes

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