1-Bromopropane → 10-Propyl-dibenz(b,f)(1,4)thiazepin-11-(10H)-one

Participants

Reaction Conditions

Reaction Steps

0.14 grams of a 50% dispersion of sodium hydride in mineral oil was added to a solution of dibenz[b,f][1,4]thiazepin-11(10H)-one in 10 ml of dimethylformamide. After 15 minutes the mixture was warmed to 50° C. and stirred under argon for one hour. After allowing the mixture to cool to room temperature, 0.34 grams of 1-bromopropane was added slowly. The reaction mixture was stirred for 5 hours, after which time it was quenched with water and the product extracted with diethyl ether. The extracts were washed with a saline solution, dried (anhydrous magnesium sulfate) and concentrated to give a colorless oil which was purified by column chromatography (ethyl acetate/hexane, 5%, 10%, 20%) to provide 0.37 grams (91% of theory) of 10-n-propyl-dibenz[b,f][1,4]thiazepin-11(10H)-one as a white crystalline solid, m.p. 103°-104.5° C.

Provenance & Evidence