Reaction #2200576

Reaction equation

sodium carbonate

N,N,3,3-tetramethylbutylamine

1-bromo-3,3-dimethylbutane

isopropanol

→

N,N-dimethyl-N,N-di(3,3-dimethylbutyl)ammonium bromide

Solvents

diethyl ether

Conditions

Workup

1. 1
   Otheris prepared
2. 2
   workup.WAITA white solid appears, and after this period
3. 3
   Temperatureto increase the amount of precipitate
4. 4
   OtherThe isopropanol and the diethyl ether are then evaporated at 30° C. by means of a rotary evaporator
5. 5
   OtherThe organic product that is formed
6. 6
   Extractionis extracted from the reaction mixture by means of dichloromethane
7. 7
   ExtractionThree successive extractions with 10 ml of dichloromethane
8. 8
   OtherThe organic phase that is obtained
9. 9
   Otheris evaporated by means of a rotary evaporator
10. 10
    OtherThe white solid that is formed
11. 11
    Washis washed with dry diethyl ether
12. 12
    Filtrationfiltered on a nylon membrane (Ø=0.2 μm)

Procedure

A mixture that contains 1 g (0.77.10−2 mol) of N,N,3,3-tetramethylbutylamine (Aldrich) and 1.917 g (1.16.10−2 mol) of 1-bromo-3,3-dimethylbutane (Prolabo) and about 4 ml of isopropanol is prepared. 1.23 g (1.16.10−2 mol) of sodium carbonate is then added. This suspension is brought to reflux for 2 days at the temperature of 100° C. A white solid appears, and after this period, about 5 ml of diethyl ether is added to the reaction mixture so as to increase the amount of precipitate. The isopropanol and the diethyl ether are then evaporated at 30° C. by means of a rotary evaporator. The organic product that is formed is extracted from the reaction mixture by means of dichloromethane. Three successive extractions with 10 ml of dichloromethane are carried out. The organic phase that is obtained is evaporated by means of a rotary evaporator. The white solid that is formed is washed with dry diethyl ether and filtered on a nylon membrane (Ø=0.2 μm). 0.8 g (0.27.10−2 mol) of N,N-dimethyl-N,N-di(3,3-dimethylbutyl)ammonium bromide (DMDMBA-Br) is then obtained. The nature of the radical that is obtained was verified by nuclear magnetic resonance of the proton; the results of this analysis are provided below. NMR 1H (D2O, 400 MHz, 25° C., δ ppm /TMS): 0.83 (s, 18H), 1.51-1.55 (m, 4H), 2.91 (s, 6H), 3.18-3.23 (m, 4H).

Source