Water → 2-[2-(1-Azetidinyl)ethyl]-7-chloro-2,3-dihydro-4,8-dimethylpyrido[3,2-f]-1,4-oxazepin-5(4H)-one oxalate

Participants

Reaction Steps

To a solution of 5.0 g (0.017 mole) of 7-chloro-2-(2-chloroethyl)-2,3-dihydro-4,8-dimethylpyrido[3,2-f]-1,4-oxazepin-5(4H)-one in 20 ml of dimethyl sulfoxide was added ~7 g of sodium carbonate (crushed) and 2.46 g (0.043 mole) of azetidine. The reaction mixture was stirred for 2 days at room temperature and poured into 200 ml of water. The aqueous mixture was extracted with 3×100 ml of benzene. The combined benzene extracts were washed with 2×100 ml of water, dried over sodium sulfate, filtered and concentrated by rotary evaporation. The residue was treated with oxalic acid in isopropyl alcohol which gave 5 g (73%) of white analytically pure crystals, m.p. 191°-92° C.

Provenance & Evidence