Tetrahydrofuran → Diallylmethyldodecylammonium Bromide

HRID 1245236Notes

Reaction equation

HRID 1245236 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][CH2:19][CH2:20][CH3:21].O1CCCC1>C(OCC)C>[Br-:9].[CH2:1]([CH:4]([NH2+:8][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH3:10])[CH2:5][CH:6]=[CH2:7])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 89191-BromododecaneHCID 12791689Hepta-1,6-dien-4-amine

Product 1

HCID 86593797Diallylmethyldodecylammonium BromideYield 20.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
65 °C

Procedure

To a 2 L Morton flask was added diallylmethylamine (100 g), 1-bromododecane (249 g), and tetrahydrofuran (750 mL). The mixture was heated to 65° C. for 44 h, and then allowed to cool to room temperature. The solvent was removed by rotary vacuum evaporation to leave two layers. Diethylether (500 mL) was added and the mixture was stirred for 1 hr. The mixture was allowed to settle and the top layer was decanted and discarded. Additional diethylether (500 mL) was added. The mixture was stirred for 24 h, and the top layer was again decanted and discarded. The remaining oil was dried in a vacuum oven at 65° C. for 4 days to yield 67 g of product.

Workup

  1. temperatureto cool to room temperature
  2. customThe solvent was removed by rotary vacuum evaporation
  3. customto leave two layers
  4. customthe top layer was decanted
  5. additionAdditional diethylether (500 mL) was added
  6. stirringThe mixture was stirred for 24 h
  7. customthe top layer was again decanted
  8. customThe remaining oil was dried in a vacuum oven at 65° C. for 4 days

Sources & evidence

ORD record
ord-6680a80ce85e4c56af495c29bba2324e
Source dataset
uspto-grants-2006_10
Patent number
US07125547B2

Reaction notes

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