Nitrogen → N-(2-(Dimethylamino)ethyl)acridine-4-carboxamide

Participants

Reaction Steps

A solution of methyl acridine 4-carboxylate (1.83 g, 7.72 mmol) and N,N-dimethylethylenediamine (3.40 g, 38.6 mmol) in n-propanol (80 ml) was flushed with N2, and the mixture was heated at reflux for three days under N2. Solvent was then removed under reduced pressure, and the residue was partitioned between CH2Cl2 (100 ml) and 1M Na2CO3 (100 ml). The organic layer was evaporated and the residue chromatographed on alumina, eluting with CH2Cl2 /MeOH (199:1) to give N-[2-(dimethylamino)ethyl]acridine-4-carboxamide (DACA) (1.47 g, 61%), mp (dihydrochloride salt from MeOH/EtOAc) 162-165° C.

Provenance & Evidence