Sodium Hydroxide → HCID 14075467, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 14.43 g (0.0632 mole) of 2-[(diethylamino)-methyl]-1-piperidine acetic acid and 2.0 g of a 75% sodium hydride dispersion in liquid paraffin in 160 ml of dimethyl formamide was heated at 50° to 80° C. until evolution of hydrogen had stopped. 15.35 g (0.0625 mole) of 9-chloro-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one were added to the resulting sodium salt of the said acid, and, at -10° C., 9.9 g (0.0646 mole) of phosphorus oxychloride were added dropwise within 10 minutes. The mixture was stirred at -10° C. for 4 hours, at 0° C. for 4 hours and at room temperature for 20 hours. The mixture was stirred into 300 g of ice, the pH was adjusted to 9 with sodium hydroxide solution, and the mixture was exhaustively extracted with dichloromethane. The combined organic phases were washed once with a little ice-water, dried over sodium sulphate and evaporated. The residue was recrystallised from acetonitrile using active charcoal. Colourless crystals of m.p. 167.5-169° C., according to the thin-layer chromatogram, mixed melting point, IR, UV and 1H NMR spectrum completely identical to a sample were obtained as in Example 2. Yield: 5.1 g (18% of theory).

Provenance & Evidence