Hydrochloride Liquid

Charge 600 mL of item 10 in a stainless steel vessel and bring to boil, cool to 40° to 50°C. 

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CgHjiN. Liquid, b.p. 79 C. Used as the hydrochloride, C HnN HCI, with m.p. 164°C. Tranylcypromine is an inhibitor of monamine oxidase and is administered orally in the treatment of depressive illness. 

Place 80 g, of hydroxylamine sulphate (or 68-5 g. of the hydrochloride), 25 g. of hydrated sodium acetate, and 100 ml. of water in a 500 ml. flask fitted with a stirrer and a reflux water-condenser, and heat the stirred solution to 55-60°. Run in 35 g (42 nil,) of -hexyl methyl ketone, and continue the heating and vigorous stirring for ij hours. (The mixture can conveniently be set aside overnight after this stage.) Extract the oily oxime from the cold mixture twice with ether. Wash the united ethereal extract once with a small quantity of water, and dry it with sodium sulphate. Then distil off the ether from the filtered extract, preferably using a distillation flask of type shown in Fig. 41 (p. 65) and of ca, 50 ml, capacity, the extract being run in as fast as the ether distils, and then fractionally distil the oxime at water-pump pressure. Collect the liquid ketoxime, b.p. 110-111713 mm. Yield, 30-32 g. 

Chill the concentrated solution of the amine hydrochloride in ice-water, and then cautiously with stirring add an excess of 20% aqueous sodium hydroxide solution to liberate the amine. Pour the mixture into a separating-funnel, and rinse out the flask or basin with ether into the funnel. Extract the mixture twice with ether (2 X25 ml.). Dry the united ether extracts over flake or powdered sodium hydroxide, preferably overnight. Distil the dry filtered extract from an apparatus similar to that used for the oxime when the ether has been removed, distil the amine slowly under water-pump pressure, using a capillary tube having a soda-lime guard - tube to ensure that only dry air free from carbon dioxide passes through the liquid. Collect the amine, b.p. 59-61°/12 mm. at atmospheric pressure it has b.p. 163-164°. Yield, 18 g. 

The leagent may also be prepared by dissolving 1 ml. of phenylhydrazine in a solution of 1 ml. of glacial acetic acid and 10 ml. of water. This procedure is not so convenient as that from the solid hydrochloride becaiise of the poisonous character of phenylhydrazine (both liquid and vapour). If the liquid is accidentally spilled on the skin, wash it at once with dilute acetic acid, followed by soap and water. 

Solubility in 5 per cent, hydrochloric acid. Add the acid to 0 10 g. of the solid or 0 20 ml. of the liquid in quantities of 1 0 ml. until 3 0 ml. have been introduced. Some organic bases (e.g., p-naphthylamine) form hydrochlorides that are soluble in water but are precipitated by an excess of acid if solution occurs at any time, the unknown is assigned to Group IV. If the compound appears insoluble, remove some of the supernatant liquid by means of a dropper to a semimicro test-tube (75 X 10 mm.), and add 5 per cent, sodium hydroxide solution until basic and observe whether any precipitate is produced the formation of a precipitate will place the compound in Group IV. 

Separations based upon differences in the chemical properties of the components. Thus a mixture of toluene and anihne may be separated by extraction with dilute hydrochloric acid the aniline passes into the aqueous layer in the form of the salt, anihne hydrochloride, and may be recovered by neutralisation. Similarly, a mixture of phenol and toluene may be separated by treatment with dilute sodium hydroxide. The above examples are, of comse, simple apphcations of the fact that the various components fah into different solubihty groups (compare Section XI,5). Another example is the separation of a mixture of di-n-butyl ether and chlorobenzene concentrated sulphuric acid dissolves only the w-butyl other and it may be recovered from solution by dilution with water. With some classes of compounds, e.g., unsaturated compounds, concentrated sulphuric acid leads to polymerisation, sulphona-tion, etc., so that the original component cannot be recovered unchanged this solvent, therefore, possesses hmited apphcation. Phenols may be separated from acids (for example, o-cresol from benzoic acid) by a dilute solution of sodium bicarbonate the weakly acidic phenols (and also enols) are not converted into salts by this reagent and may be removed by ether extraction or by other means the acids pass into solution as the sodium salts and may be recovered after acidification. Aldehydes, e.g., benzaldehyde, may be separated from liquid hydrocarbons and other neutral, water-insoluble hquid compounds by shaking with a solution of sodium bisulphite the aldehyde forms a sohd bisulphite compound, which may be filtered off and decomposed with dilute acid or with sodium bicarbonate solution in order to recover the aldehyde. 

Aminoselenazoles are crystalline compounds, and with the exception of the nonsubstituted derivative (1) they are stable and practically odorless. They are more basic than 2-aryl- or 2-alkylselenazoles. The hydrochlorides are not easily hydrolyzed in aqueous solution. Some of the K-substituted compounds are oily liquids. 

Dissociation extraction is the process of using chemical reac tion to force a solute to transfer from one liquid phase to another. One example is the use of a sodium hydroxide solution to extract phenolics, acids, or mercaptans from a hydrocarbon stream. The opposite transfer can be forced by adding an acid to a sodium phenate stream to spring the phenolic back to a free phenol that can be extrac ted into an organic solvent. Similarly, primary, secondary, and tertiary amines can be protonated with a strong acid to transfer the amine into a water solution, for example, as an amine hydrochloride salt. Conversely, a strong base can be added to convert the amine salt back to free base, which can be extracted into a solvent. This procedure is quite common in pharmaceutical production. 

Dissolved in distilled water and excess of 6M NaOH was added to give pH 12. The organic phase was separated and extracted with four volumes of diethyl ether. The combined extracts were filtered through paper to remove water and the solvent evaporated. The dark brown residual liquid was kept under high vacuum [Vaidya and Matbias J Am Chem Soc 108 5514 1986]. It can be distd but readily darkens and is best kept as the hydrochloride [7379-35-3] M 150.1, m 163-165°(dec). 

Dried with Linde type 5A molecular sieves, BaO or sodium, and fractionally distd. The distillate (200g) was heated with benzene (500mL) and cone HCl (150mL) in a Dean and Stark apparatus on a water bath until water no longer separated, and the temperature just below the liquid reached 80°. When cold, the supernatant benzene was decanted and the 2,4-lutidine hydrochloride, after washing with a little benzene, was dissolved in water (350mL). After removing any benzene by steam distn, an aqueous soln of NaOH (80g) was added, and the free... 

Recrystd from Me2CO, H2O or Et0H-Et20 and dried. Soluble in H2O (60%) and EtOH (5%) but insol in Et20 and slightly in CHCI3. The hydrochloride has m 300 (from Mc2CO). The free base is a viscous liquid which forms a crystalline hydrate with m 59 and [a] -28° (c 2.7, H2O). Readily hydrolysed in dilute acid or base. [Meinwald J Chem Soc 712 7953 Fodor Tetrahedron 1 86 1957.]... 

MethyHsopelletierine, CgHj,ON. This base, isolated by Piccinini under the name fsomethylpelletierinc, was re-examined by K. Hess ei al. It is an oily alkaline liquid, b.p. 114-7°/26 mm., miscible with water and optically inactive. The hydrochloride has m.p. 156° hydrobromlde, m.p. 151-2° the picrate melts at 158° and the aurichloride forms orange-yellow rosettes, m.p. 115-7°. The base can be resolved into d- and... 

Z-Ecgonine, CgHigOgN. HjO. This substance was first obtained I Lossen as the final basic hydrolytic product of the action of acids c cocaine, and is obtainable in like manner from several of the alkaloii occurring with cocaine (see above). It crystallises from dry alcohol i monoclinic prisms, m.p. 198° (dec.), 205° (dry), [a]n — 45-4°, is soluble i water, sparingly so in alcohol, insoluble in most organic liquid Eegonine forms Salts with bases and acids the hydrochloride crystallis... 

Ephedrine also oeeurs in the leaves of the yew tree [Taxus baccata) and in Sida rhombifolia Linn, whilst Stockman s cathine from Catha edulis Forsk has been shown by Wolfes to be d-nor- -ephedrine. Ghosh, Chopra and Dutt state that the bark of Moringa pterygosperma Gaertn. contains two alkaloids similar to ephedrine in pharmacological action. The more active of the two, moringinine, is amorphous the other is a liquid but jdelds a crystalline hydrochloride, C,H. HCl, m.p. 254-4°, + 1-8°, a picrate, m.p. 195°, and an aurichloride, m.p. 170-8°. 

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