Ethylamine, 1-Methyl

It is also common and correct to name amines with each alkyl branch listed as an attachment before the suffix -amine. In this system of nomenclature, the molecules in Figure 1.16 are ethylamine, methyl ethyl amine, and methyl diethyl amine. Several other methods of naming amines exist, but they will not be covered in this course. 

A mixture of N-benzyl-2-(2-methoxyphenoxy)ethylamine, methyl ethyl ketone, and 5-bromoacetyl-2-methylbenzenesulfonamide was refluxed with stirring. After cooling the reaction mixture, ethyl ketone was distilled off under reduced pressure and the residue formed was dissolved in benzene. Then, ether was added to the solution and after removing the hydrobromide of N-benzyl-2-(2-methoxyphenoxy)ethylamine precipitated, the solvent was distilled off under reduced pressure to provide a viscous oily product. 

Orthorhombic, bisphenoidal prisms from ale, dec 103-105. Sweetest of the sugars. Shows mutarotation. Mg — 132 — —92 (c = 2). Rapid and anomalous mutarota tion involves pyranose-furanose interconversion. The final value is obtained instantly in the presence of hydroxyl ions. Ka at 18" 8.8 x l0-u. Freely sol in water. One gram dissolves in 15 ml ale, in 14 ml methanol. Slightly sol in cold, freely in hot acetone sol in pyridine, ethylamine, methyl-amine. 

Startg. m. stirred 18 hrs. at 40° in methanol containing a small amount of tri-ethylamine -> methyl N-lauroyl-a-methylthiovalinate (Y ca. 100%) treated ca. 1 day at room temp, with cuprous chloride in methanol -> methyl N-lauroyl-a-methoxyvalinate (Y 93%). F. e. s. K. Ogura et al., Chem. Lett. 1975, 803. 

Schatzmann, in 1891, tried to prepare 2-thiazolines by hydrogenation of thiazoles and by the action of sodium and ethanol on 2,4-dimethyl-thiazole, 2-methylthiazole, and 2-methyl-4-phenylthiazole (476). None of these substrates was reduced to thiazoline the second gave no reaction and the first underwent ring cleavage, leading to a mixture of n-propylmercaptan and ethylamine (Scheme 90). Three years later the same... 

Sodium is soluble in ethylenediamine (16,17), but solubiHty in other amines such as methyl- or ethylamine may require the presence of ammonia. Sodium solubiHty in ammonia and ethylenediamine solutions has been extensively investigated (18). Sodium is insoluble in most hydrocarbons and is... 

Anhalonine and Lophophorine. Spath and Gangl showed that each of these alkaloids contains a methylenedioxy group and that the quarternary iodide prepared from dZ-anhalonine is identical with lophophorine methiodide so that lophophorine must be N-methylanhalonine. Anhalonine was synthesised from 3 4-methylenedioxy-5-methoxybenzaldehyde by condensation with nitromethane, reduction of the product to the corresponding -ethylamine, the acetyl derivative (VII) of which, on treatment with phosphoric anhydride, condensed to 6-methoxy-7 8-methylenedioxy-l-methyl-3 4-dihydrofsoquinoline, m.p. 60-2°. This, on reduction, furnished the corresponding tetrahydrofsoquinoline, which proved to be anhalonine (VIII), and on conversion to the quaternary methiodide the latter was found to be lophophorine (IX) methiodide. The possible alternative, 8-methoxy-6 7-methylenedioxy-l 2-dimethyl-l 2 3 4-tetrahydrofsoquinoline, was prepared by Freund s method and the methiodide shown not to be identical with lophophorine methiodide. 

The reactions of (174) with various amines has been studied." " Hydrolysis of the hexamine salt of (174) gave not the symmetric diamine but (184) via a cyclic intermediate. The pyrolysis of 5-methyl-2-thenyltrimethyl ammonium hydroxide (185) is claimed to give (186) through a 1,6 Hofmann elimination reaction. The Bischler-Napieralski cyclization has been applied to acetyl derivatives of 2-(2-thienyl) ethylamine and 2-(3-thienyl) ethylamine for the preparation of sulfur analogs of isoquinoline. ... 

When diazomethane is slowly added to excess lactam, the anions formed can interact with unreacted lactam by means of hydrogen bonds to form ion pairs similar to those formed by acetic acid-tri-ethylamine mixtures in nonpolar solvents. The methyldiazonium ion is then involved in an ion association wdth the mono-anion of a dimeric lactam which is naturally less reactive than a free lactam anion. The velocity of the Sn2 reaction, Eq. (7), is thus decreased. However, the decomposition velocity of the methyldiazonium ion, Eq. (6a), is constant and, hence, the S l character of the reaction is increased which favors 0-methylation. It is possible that this effect is also involved in kinetic dependence investigations have shown that with higher saccharin concentrations more 0-methylsaccharin is formed. 

Progressive departure from the fundamental structure of the lead agent cimetidine led to the anti ulcer agent oxmetidine (47). The synthesis involves -methylation (CH3I) of the 2-thiouracil intermediate and is followed by an addition-elimination reaction with 2-(5-methyl-4-imidazolylmethylthio) ethylamine to give oxmetidine (47). ... 

Chloroethy I )-theophy II ine Qi-Methyl-)S ihenyl ethylamine Hydrogen chloride... 

D) 4 -[N-Ethyi-1 "-Methyl-2 -(4" -Methoxyphenyl)Ethylamino]Butyi-3,4-Dimethoxybenzoate Hydrochloride 10.3 g of 4 -iodobutyl-3,4-dimethoxybenzoate and 11.0 g of N-ethyl-p-methoxyphenylisopropylamine (obtained by catalytic reduction of an alcoholic solution of an excess quantity (60%) of p-methoxy-phenyl-acetone, to which was added a 33% (weight-for-weight) aqueous solution of ethylamine, with Pt as a catalyst), were boiled in 200 ml of methyl ethyl ketone for 20 hours, cooled and the iodine ion was determined the reaction was found to be complete. Then the methyl ethyl ketone was evaporated in vacuo and the residue was dissolved in 300 ml of water and 30 ml of ether the layers were separated and the water layer was extracted twice more with 20 ml portions of ether. 

Common Name N-demethylorphenadrine hydrochloride N-methyl-2[o -(2-tolybenzyl)oxy]-ethylamine hydrochloride... 

Ether, chloromethyl methyl [Methane, chloromethoxy-], 97 Ethylamine, dusoptopyl- [ 2-Propanamme, Af-ethyl-Af-(l-methylethyl)-], 59 Ethylamine, 2-(3,4-dimethoxyphenyl)-[Ben-zeneethanamme, 3,4-dimethoxy-], 5 Ethylene, 1,1-diphenyl- [Benzene, 1,1 -ethenylidenebis-], 32 Ethylene, tetramethyl- [2-Butene, 2,3-dimethyl-], 35... 

Ethylamine, a-(l-naphthyl)- [1-Naphtlulene-methylamine, a-methyl-], racemic,... 

Ethanamme, 2-(diphenylmethoxy)-jV,vV-di-methyl- [Ethylamine, (2-diphenyl-methoxy)-A,Ar-dimethyl-, Diphenhydramine], 55, 3, 4... 

Ethoxylcarbonyl-2-arylazo-2-nitroe thane derivatives lb 365 Ethoxyquine la 106,108 Ethylamine lb 104,268 N-Ethylamine derivatives, tertiary lb 290 Ethylamphetamines la 45 N-Ethyl-N -benzylthiourea lb 301 N-Ethyl derivatives lb 190 -, secondary lb 190 -, tertiary lb 188, 191 Ethelenediamine la 392 Ethylene glycol dinitrate lb 415 N4-Ethyl-N4-(2-methanesulfonamido-ethyl)-2-methyl-l,4-phenylenediamine, reagent la 368... 

Phenyl N-acetylcarbazate 1529 cyclizes on boiling with excess TCS 14/tri-ethylamine in toluene to give 5-methyl-l,3,4-oxadiazohne-2-one 1530 in 65-70% yield [41, 59, 60]. The same type of cyclization was subsequently described for re-... 

The molecular modelling approach, taking into account the pyruvate—cinchona alkaloid interaction and the steric constraints imposed by the adsorption on the platinum surface, leads to a reasonable explanation for the enantio-differentiation of this system. Although the prediction of the complex formed between the methyl pyruvate and the cinchona modifiers have been made for an ideal case (solvent effects and a quantum description of the interaction with the platinum surface atoms were not considered), this approach proved to be very helpful in the search of new modifiers. The search strategy, which included a systematic reduction of the cinchona alkaloid structure to the essential functional parts and validation of the steric constraints imposed to the interaction complex between modifier and methyl pyruvate by means of molecular modelling, indicated that simple chiral aminoalcohols should be promising substitutes for cinchona alkaloid modifiers. Using the Sharpless symmetric dihydroxylation as a key step, a series of enantiomerically pure 2-hydroxy-2-aryl-ethylamines... 

Aldrich and used for all oxidation experiments. TEMPO, sodium hydroxide, sodium sulfide, formaldehyde, ethylamine and methyl-a-D-glucopyranoside were reagent grade or higher and were used as received from Sigma and Aldrich. 

Dobutamine (76), on the other hand, is a dopamine derivative which does not act centrally, but is of interest because of its coronary vasodilator properties. Such drugs are potentially of value in treatment of angina pectoralis. Further, it is now undergoing extensive clinical trials as an inotropic agent for use in heart failure. Its synthesis is effected by Raney nickel catalyzed reduction of methyl p-methoxyvinylphenylketone (75) to its dihydro analog followed by reductive alkylation with p-(3,4-dimethoxyphenyl)ethylamine. The ether groups are cleaved with HBr to complete the synthesis of... 

Preparation of the quaternary anticholinergic agent benzilonium bromide (47) is begun by conjugate addition of ethylamine to methylacrylate, giving aminoester 42. Alkylation of 42 with methyl bromo-acetate leads to diester 43, which is transformed into pyrrolidone 44 by Dieckmann cyclization, followed by decarboxylation. Reduction of 44 by lithium aluminum hydride leads to the corresponding amino-alcohol (45). Transesterification of alcohol 45 with methyl benzilate leads to 46. Benzilonium bromide (47) is obtained by alkylation of ester 46 with ethyl bromide. 2... 

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