Phenethyl bromide → HCID 11432173, compound

Participants

Reaction Conditions

Reaction Steps

18 g of ethyl 5-(2-chlorophenyl)-1,2,3,6,7,9-hexahydro-2-oxo-8H-pyrido[4′,3′:4,5]thieno[2,3-e]-1,4-diazepine-8-carboxylate (4.46 mmol) is solubilized under argon, in 180 ml of anhydrous dimethylformamide. Sodium hydride at 60% (1.784 g, 4.46 mmol) is added then the reaction medium is heated for approximately 30 minutes at 50° C. until there is no more release. The reaction medium is cooled down to a temperature around 20° C. then 2-bromoethylbenzene (6.2 ml, 4.46 mmol) is added with a syringe. Agitation is carried out for 16 hours at 23° C. then the reaction medium is poured into a saturated solution of ammonium chloride (400 ml). Extraction is carried out with ethyl acetate (2×500 ml). The organic phase is dried over magnesium sulphate then the solvent is evaporated off with a rotary evaporator. After purification by chromatography on a silica column (eluent ethyl acetate-heptane: 0-100 to 20-80), the fractions containing only the product are evaporated and the desired product is obtained in the form of a white amorphous powder (20.3 g, 89%).

Provenance & Evidence