Ethyl chloroformate → HCID 21442798, compound

Participants

Reaction Steps

A mixture of 5-(4-benzyl-2-morpholinylmethyl)-10,11-dihydro-5H-dibenz[b,f]azepine (1.62 g) and ethyl chloroformate (1.44 g) in benzene was stirred under reflux for 8 hours. The reaction mixture was cooled, admixed with 10% aqueous sodium hydroxide and extracted with benzene. The benzene extract was dried over anhydrous sodium sulfate and evaporated to afford 5-(4-ethoxycarbonyl-2-morpholinylmethyl)-10,11-dihydro-5H-dibenz[b,f]azepine as an oily substance. To a solution of the oil in ethanol was added 30% aqueous sodium hydroxide, and the resulting mixture was stirred at 65° C for 5 hours. The reaction mixture was cooled and extracted with benzene. The benzene extract was dried over anhydrous sodium sulfate and evaporated to afford 5-(2-morpholinylmethyl)-10,11-dihydro-5H-dibenz[b,f]azepine as an oily substance. M.P. 194.5°-195.5° C (oxalate).

Provenance & Evidence