Teniloxazine
Teniloxazine, also known as sufoxazine and sulfoxazine, is a drug which is marketed in Japan. Though initially investigated as a neuroprotective and nootropic agent for the treatment of cerebrovascular insufficiency in the 1980s, it was ultimately developed and approved as an antidepressant instead. It acts as a potent norepinephrine reuptake inhibitor, with fair selectivity over the serotonin and dopamine transporters, and also behaves as an antagonist of the 5-HT2A receptor.
Synthesis
Amide formation between 1--3-propan-2-ol and Chloroacetylchloride gives PC13682456. In the presence of sodium metal closing of the ring morpholine occurs to give PC13682470. Lactam reduction with lithium aluminium hydride affords 4-Benzyl-2-morpholine . Treatment with Ethyl chloroformate gives the urethane and hence 4-Ethoxycarbonyl-2-morpholine, PC21482171. Hydrolysis of the carbamate in the presence of barium hydroxide completes the synthesis of Teniloxazine.Alternately, base reaction between 1--2,3-epoxypropane and 2-Aminoethyl hydrogen sulfate is another way to perform the synthesis.