N-Benzylethylenediamine may be used for the synthesis of N-benzyl-N,N′,N′-tris(tert-butyloxycarbonylmethyl)ethylenediamine and 3-benzyl-2-(phenyl-2-sulfonate)-2-imidazoline tetraheptylammonium salt.
N-Benzylethylenediamine participates in the one-pot synthesis of N,N,N′-trisubstituted guanidines. It undergoes condensation with dibenzoylmethane (1,3-diphenyl-1,3-propanedione) in stoichiometric ratio 1:1 to afford the corresponding Schiff monobase.
Ethylenediamine (3.4 mL, 51 mmol) with anhydrous methanol (38 mL) was added to a 100 mL aubergine vial. Benzaldehyde (1000 μL, 9.8 mmol) was dissolved in anhydrous methanol (5 mL) and slowly added dropwise into the above aiguille. After the dropwise addition, the reaction mixture was continued to be stirred for 30 min. Subsequently, sodium borohydride (0.371 g, 11 mmol) was added in batches under ice bath conditions. The reaction mixture was cooled and stirred overnight. Upon completion of the reaction, the solvent was removed by evaporation and dichloromethane (50 mL) was added to dissolve the residue. The organic phase was washed twice with saturated saline (5 mL) and the organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated to give N-benzylethylenediamine (colorless liquid, 938 mg, 64% yield).
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