3-Phenylprop-2-Enal → N,N'-Dicinnamylidene-1,6-hexanediamine

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Reaction Steps

Cinnamaldehyde (198.2 g, 1.5 mole) is carefully added to a solution of 1,6-hexanediamine (87.2 g, 0.75 mole) in toluene (400 ml). Slight exotherm to 60° C. is observed. The resulting solution is heated at reflux until water (27 ml, 1.5 mole) is evolved. Evaporation of the solution gives 250.7 g of a brown viscous oil. 1H NMR: δ 1.0-2.85 (broad bands 8H); δ 3.6 (triplet 4 H); δ 6.82-8.22 (broad multiplete 16 H). Elemental analysis: Theory for C24H28N2 : C,83.72; H,8.14; N,8.14%. Found: C,83.61; H,8.35; N,8.05%.

Provenance & Evidence