Trimetozine

Chemical Name 4-(3,4,5-Trimethoxybenzoyl)morpholine Common Name — 

46 g 3,4,5-trimethoxybenzoyl chloride are dissolved in 300 ml anhydrous benzene and 25 g triethylamine and thereafter 1 9 g anhydrous morpholine are added in small portions with icecooling. The solution is boiled for 2 hours under reflux. The precipitate is filtered off, and the solution is washed with dilute sulfuric acid, then with sodium hydrogen carbonate solution and finally with water,and then evaporated. The residual yellow oil soon crystallizes the crystalline mass of the desired material is taken up with ether, filtered and then recrystallized from 90% ethanol, from which it separates in prisms. It is slightly soluble in water. Yield 80%, melting point 120°C to 122°C. 

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Because FIC1 is formed during the reaction, two equivalents of the amine must be used. One equivalent reacts with the acid chloride, and one equivalent reacts with the HC1 by-product to form an ammonium chloride salt. If, however, the amine component is valuable, amide synthesis is often carried out using 1 equivalent of the amine plus 1 equivalent of an inexpensive base such as NaOH. For example, the sedative trimetozine is prepared commercially by... 

Problem 21.11 i Write the mechanism of the reaction just shown between 3,4,5-trimethoxybenzoyl chloride and morpholine to form trimetozine. Use curved arrows to show the electron flow in each step. 

C10H11CIO4 4521-61-3) see Dilazep Hexobendine Trimethobenzamide Trimetozine Troxipide... 

Triazuril, 305 Tricetamide, 94 Triclonide, 198 Triflocin, 282 Triflubazam, 406 Triflumidate, 98 Trilostane, 158, 159 Trimazosin, 382 Trimethoprim, 302 Trimetho< inol, 374 Trimetozine, 94 Trimoxamine, 49 Trip, 476... 

C 0IIMClO4 4521-61-3) see Dilazcp Hcxobendinc Trimetliobenzamide Trimetozine Troxipide 23,4-trimethoxybenzyl chloride (C 0H, CIO2 1133-49-9) see Trimetazidine... 

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. 

Biperiden, debrisoquine, methyl benzoquate, oxethazaine, phenprobamate, trimetozine, tripelennamine Benethamine (-> brown), clomocycline, nortriptyline Ritodrine, thymoxamine, triacetyloleandomycin, tylosin Alcuronium, bufotenine, psilocin... 

Etilefrine Hydrochloride Octamylamine Hydrochloride l -Progesterone Trimetozine... 

Trimethyltrifluoromethylphenothiazinylpropylamine, 1043 Trimethyltrioxane, 851 Trimetozine, 1050 Trimipramine, 1051 test on stomach contents, 6 test on urine, 5 Trimipramine maleate, 1051 Trimogal, 1049 Trimolide, 1050 Trimone Sublets, 598,773 Trimopan, 1049 Trimovate, 476 Trimox, 348 Trimpex, 1049 Trimstat, 876... 

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