Acetic Acid → HCID 22342993, compound

Participants

Reaction Steps

A suspension of 2-[3-(benzylamino)benzyl]-3,6-piperazinedione (0.45 g), 37% aqueous formaldehyde (81 mg), sodium triacetoxyborohydride (0.62 g) and acetic acid (175 mg) in a mixture of 1,2-dichloroethane (15 ml) and N,N-dimethylformamide (5 ml) was stirred for 5 hours at room temperature. Then additional 37% aqueous formaldehyde (0.1 ml), acetic acid (0.2 ml) and sodium triacetoxyborohydride (0.60 g) were added to the reaction mixture and the whole was stirred for further 2 hours. The mixture was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel using a mixture of dichloromethane and methanol (10:1). The fractions containing the objective compound were collected and evaporated under reduced pressure. The resulting precipitates were collected by filtration and washed with isopropyl alcohol to give 2-[3-(N-benzyl-N-methylamino)benzyl]-3,6-piperazinedione (0.46 g) as colorless crystals.

Provenance & Evidence