Ethyl Acetate → 6-Benzyl-1,4-diazepan-6-ylamine

Participants

Reaction Steps

In a 500 ml flask, compound 5 (16.0 g, 38.5 mmol) was dissolved in methanol (100 mL); Pd/C (10%, 3.0 g, moistened with 0.5 ml water) was added at once followed by ammonium formate (24.0 g, 0.385 mol). The mixture was stirred and heated to reflux for 3 h. When the reaction is complete (TLC PET/AcOEt 9/1), the catalyst was removed by filtration on Celite®, and the filtrate evaporated in vacuo. The residue is redissolved in dichloromethane and washed with 5% aq. NaOH. The organic phase was then dried (Na2SO4) obtaining 6 (5.98 g, 76%) as light yellow oil. M.p.: ESI-MS: 206 (MH+); (Calc. for C12H19N3: 205 u.m.a.).

Provenance & Evidence