General procedure for the synthesis of tris(dimethylaminopropyl)hexahydrotriazine from formaldehyde and N,N-dimethyl-1,3-diaminopropane: To a 125 mL round-bottomed flask was added a solution of N,N-dimethylpropane-1,3-diamine (6.29 mL, 50 mmol) in toluene (15 mL), followed by paraformaldehyde (1.652 g, 55 mmol, 1.1 eq.) . A Dean-Stark manifold was installed and the reaction mixture was refluxed for 1.5 hours. After completion of the reaction, toluene was removed by evaporation. A portion of the residue (1.9757 g) was taken and partitioned between chloroform (15 mL) and water (5 mL). The organic layer was separated, dried over anhydrous magnesium sulfate and concentrated to give a clarified oily product. The product yield was 66% (1.3067 g). Thin layer chromatography (TLC) analytical conditions: unfolding agent was a 20% ethyl acetate solution of methanol (10 mL) with an Rf value of 0.05. Nuclear magnetic resonance hydrogen spectrum (1H NMR, 400 MHz, CDCl3, δ): 3.29 (broad peak, 6H, H5), 2.40 (triple peak, 6H, J = 7.5 Hz, H4), 2.25 (triple peak, 6H, J = 7.5 Hz, H3), 2.18 (single peak, 18H, H2), 1.59 (multiple peaks, 6H, J = 7.5 Hz, H1) ppm. nuclear magnetic resonance carbon spectrum (13C NMR, 100 MHz, CDCl3, δ): 74.65 (C5), 57.83 (C3), 50.78 (C4), 45.54 (C2), 25.88 ( C1) ppm.
![1,3,5-Tris[3-(dimethylamino)propyl]hexahydro-1,3,5-triazine](/CAS/GIF/15875-13-5.gif)