Trimethylamine.hydrochloride

TRIMETHYLAMINE HYDROCHLORIDE Mix 100 g. of ammonium chloride and 266 g. of paraformaldehyde in a 1-litre round-bottomed flask fitted with a long reflux condenser containing a wide inner tube (ca. 2 cm. diameter) the last-named is to avoid clogging the condenser by paraformaldehyde which may sublime. Immerse the flask in an oil bath and gradually raise the temperature. The mixture at the bottom of the flask liquefies between 85° and 106° and a vigorous evolution of carbon dioxide commences at once remove the burner beneath the oil bath and if the reaction becomes too violent remove 

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Trimethylamine hydrochloride [593-81-7] M 95.7, m >280°(dec). Crystd from CHCI3, EtOH or n-propanol, and dried under vacuum. It has also been crystd from benzene/MeOH, MeOH/diethyl ether and dried under vacuum over paraffin wax and H2SO4. Stood over P2O5. It is hygroscopic. 

Recently Tanabe and co-workers have found that several alcohols were smoothly and efficiently tosylated using tosyl chloride/triethylamine and a catalytic amount of trimethylamine hydrochloride as reagents.6 Compared with the traditional method using pyridine as solvent, this procedure has the merit of much higher reaction rates, and it avoids the side reaction in which the desired tosylate is converted into the corresponding chloride. 

At the same time the formaldehyde (as hydrate) is dehydrogenated yielding formic acid and COs. If the amount of aldehyde is increased trimethylamine hydrochloride is produced in an analogous manner. 

The treatment of terminal alkynes with telluroesters in DMF in the presence of Cul and triethylamine, followed by addition of trimethylamine hydrochloride, gives rise to (Z)-()S-aryltelluro)-a,)S-enones." °... 

Administered to mouse embryo cultures in vitro, trimethylamine was teratogenic, causing neural mbe defects and inhibiting embryonic growth. Trimethylamine may exert these effects by reducing macromolecular synthesis. Repeated intraperitoneal injections of trimethylamine hydrochloride in pregnant mice caused fetotoxicity only at maternally toxic doses. ... 

The trimethylamine may be generated by the action of alkali on trimethylamine hydrochloride and dissolved in acetone. The submitter prepared trimethylamine by the method of Som-melet and Ferrand and obtained a 65% yield by the interaction of ammonia, formaldehyde, and formic acid. The checkers found that a commercial 25% solution of trimethylamine in methanol (210 ml.) gave the same yields as the acetone solution. 

Trimethylacetic acid, 350, 351 Trimethylamine hydrochloride, 414,416 Trimethylene dibromide, 279 Trimethylene dicyanide, 407, 409 Trimethylene-di-iodide, 288 1 3 5-Trinitrobenzene, 965 addition compounds of, 519 ... 

The references to the preparation of trimethylamine are referred to in the following experiment entitled Trimethylamine Hydrochloride. ... 

To obtain the trimethylamine hydrochloride, the hydrochloric acid solution is evaporated, first over a free flame and later, when the crystals start to form, on a steam bath. As the solution gets more and more concentrated, the trimethylamine hydrochloride crystallizes out and is filtered from time to time, is dried for a few minutes in an air bath, temperature 100-110°, and is finally kept in a tightly closed bottle. If the trimethylamine hydrochloride as it crystallizes is centrifuged, the product is obtained pure and dry at once. The average yield from four runs is 710 g. of perfectly pure trimethylamine hydrochloride and 82 g. of product which is tinged slightly yellow (a total of 89 per cent theory based on the ammonium chloride). This coloration results from the evaporation to dryness of the very last portion of solution. 

The complete solubility of the product in chloroform 1 shows the trimethylamine hydrochloride to be free from ammonium chloride and methylamine hydrochloride and the fact that no precipitate is obtained when tested with sodium hydroxide and benzene sulfonyl chloride in aqueous solution shows that dimethylamine hydrochloride is absent. 

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