Hydrochloric Acid → HCID 20392271, compound

Participants

Reaction Steps

To a slurry of 3.88 g. of 4,9-dihydro-6,7,9-trimethyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one in 100 ml. of tetrahydrofuran, cooled in an ice bath and stirred under argon is added 60 ml. of 1 M borane in tetrahydrofuran, dropwise over 15 minutes. The mixture is stirred for one hour at room temperature, refluxed for 18 hours, cooled in an ice bath and decomposed by the addition of 30 ml. of 6 N hydrochloric acid. The mixture is stirred for one hour, 30 ml. of 10 N sodium hydroxide is added, stirring is continued for one hour and the tetrahydrofuran is evaporated. The remaining aqueous layer is filtered giving blue tinted crystals. These crystals are combined with 125 ml. of absolute methanol and saturated with gaseous hydrogen chloride. A 25 ml. portion of water is added and the mixture is heated on a steam bath until solution is complete. The methanol is evaporated in vacuo, 150 ml. of water is added and the solution is made basic with 10 N sodium hydroxide. The solution is extracted with methylene chloride and the extract is dried over magnesium sulfate and evaporated giving the desired product as blue crystals, mp. 121°-125° C.

Provenance & Evidence