Morpholine tranquilizer

Another important line of research was the synthesis of 3,4,5-trialkoxybenzamides, as some of these derivatives showed outstanding psychopharmacological activities. Among these compounds, 4-(3,4,5-trimethoxybenzoyl)morpholine (named Trioxazin) was introduced as a minor tranquilizer, N-cyclopropyl-4-(decyloxy)-3,5-dimethoxybenz-amide (Denegit) as an antiepileptic agent, and 2-(l-pyrrolidinyl)ethyl 4-butoxy-3,5-dimethoxybenzoate (Vasopenton) as a spasmolytic, for use in clinical practice. 

In many reactions the simple saturated nitrogen heterocycles—piperidine, pyrrolidine, piperazine, and morpholine—behave simply as secondary amines that happen to be cyclic. They do the sorts of things that other amines do, acting as nucleophiles in addition and substitution reactions. Morpholine, for example, is acylated by 3,4,5-trimethoxybenzoyl chloride to form the tranquillizer and muscle relaxant trimetozine, and N-methyl piperazine can be alkylated in an S l reaction with diphenylmethyl chloride to give the travel-sickness drug cyclizine. 

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