Formaldehyde → 1,4-Dibenzyl-6-benzyl-6-nitro-1,4-diazepane

Participants

Reaction Steps

In a 250 mL round-bottom flask N,N′-dibenzylethylenediamine diacetate (19.67 g, 54.6 mmol) and 2-nitroethylbenzene (4, 8.28 g, 54.6 mmol) are dissolved in 1:1 toluene/methanol (100 mL). Paraformaldehyde (5.74 g, 0.191 mol) is added portionwise to the solution and the resulting suspension is refluxed. The mixture becomes homogeneous (dissolution of paraformaldehyde) and after 3 h at reflux, the mixture is cooled and evaporated in vacuo. The residue is recrystallized from methanol, obtaining pure 5 (20.29 g, 89%) as light yellow solid. M.p. 83-85° C. (EtOH), ESI-MS: 438 (MNa+), 416 (MH+); (Calc. for C26H29N3O2: 415 u.m.a.).

Provenance & Evidence