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ChemicalBook CAS DataBase List TRIS(2-DIMETHYLAMINOETHYL)AMINE
33527-91-2

TRIS(2-DIMETHYLAMINOETHYL)AMINE synthesis

4synthesis methods
-

Yield:33527-91-2 26%

Reaction Conditions:

in water at 100;Cooling with ice;Inert atmosphere;

Steps:

Synthesis of Tris(2-(dimethylamino)ethyl)amine (Me6TREN)
Synthesis of Tris(2-(dimethylamino)ethyl)amine (Me6TREN)
In a 250 mL round bottom flask TREN (10.00 g, 0.07 mol) in water (25 mL) was added dropwise using a pressure equalizer to an ice chilled mixture of formaldehyde (36% in water) (39.00 g, 0.47 mol) and formic acid (55.16 g, 1.2 mol).
After complete addition of TREN, the RB was brought to an oil bath and the solution was refluxed gently overnight at 100° C.
It was cooled to room temperature and water was removed by trap-to-trap distillation.
To remove unreacted formic acid, product was dissolved in 20 mL of acetonitrile and passed through a basic alumina column.
Acetonitrile was removed by rotary evaporation and product was further purified by vacuum distillation. Yield=4.10 g (26%).
1H-NMR (CDCl3, 7.27 ppm): 2.22 (s, -CH3), 2.37 (dd, -CH2N(CH2)2), 2.60 (dd, -CH2N(CH3)2).
13C-NMR (CDCl3, 77.23 ppm): 46.1 (-CH3), 53.3 (-CH2N(CH2)2), 57.7 (-CH2N(CH3)2).

References:

The University of Akron;Pugh, Coleen R.;Singh, Anirudha US8524942, 2013, B2 Location in patent:Page/Page column 21

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