Alkyl amines ethylamine

This method is essentially that described by Pollard and Par-cell.8 No other procedure appears to have been used to prepare N-(2-bromoallyl)ethylamine. A number of N-(2-haIoaIIyl)alkyl-amines have been prepared by treatment of a 2,3-dihalopropene with a primary alkylamine in water,8-4 ether,8-4 or benzene.5... 

The results of the alkylation of ethylamine with n-butanol on CuZn/Al catalyst at different temperatures and amine/alcohol ratios are listed in Table 4. Upon increasing the reaction temperature from 175 to 205 °C at EtNH2/n-BuOH molar ratio of 1.3 the selectivity of the symmetrical secondary amine sharply increased at the expense of the mixed amine and the yield of... 

Different kinetic behavior was observed when secondary hydroxy-alkylic amines, methyl-2-hydroxyethylamine and butyl-2-hydroxy-ethylamine, were employed as nucleophiles. Autoacceleration appeared in dioxane for both secondary amines however, normal second order kinetics were followed in DMF when the nucleophile is methyl-2-hydroxyethylamine which has less bulky substituents. In the reaction of butyl-2-hydroxyethylamine with CMPS in DMF, rate retardation began when the conversion reached about 75% owing to the steric hindance of the bulky butyl groupThus the sensitivity of the rate profiles to reaction media and nucleophile structure complicates assessment of "polymeric effects". 

The reaction rate in the presence of decylamine is faster than that in the presence of ethylamine by a factor of 700. This imphes that the reactive amino group has been oriented very close to the susceptible carbonyl group of the ester by the establishment of a maximal number of hydrophobic contacts. Correspondingly, there is a decline in the reaction rate as the alkyl amine group is lengthened further. 

Chem. Desaip. N-alkyl tallow N,N bis hydroxy ethylamine and tallow alkyl amines... 

A number of 2eohtic materials have been claimed to cataly2e this reaction and reaction temperatures are on the order of 200—350°C with pressures as high as 18000 kPa (2600 psi) reported. This is a low conversion process and recycle of the unconverted starting materials is necessary to provide an economical process. Amination of ethylene to produce ethylamines cataly2ed by ammonium iodide is reported, but not beheved to be practiced commercially (15,16). Alkyl Halide Amination (Method 7). The oldest technology for pioducing amines is the reaction of ammonia with an alkyl hahde. This... 

It was only around 1850 that the first amines were discovered by Wurtz [2], who considered them as alkylated (or arylated) derivatives of NH3. Nowadays, it is well known that the amine function is widespread among biologically important compounds, but mostly it is present in polyfunctional molecules such as amino acids, alkaloids, etc. Simple amines are very rare in nature, with the exception of tri-ethylamine and the trimethylammonium ion which come from the putrefaction of proteins. 

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. 

Problem 18.8 Prepare ethylamine by (a) Gabriel synthesis, (6) alkyl halide amination, (c) nitrile reduction, (d) reductive amination, (e) Hofmann degradation. ... 

The reaction mechanism including the formation and decomposition of quaternary cations may be a general pathway in amine alkylation processes on acidic zeolites. Pouilloux et al. (247), for example, synthesized dimethylethylamine from ethylamine and methanol on an acidic catalyst. At the reaction temperature of 503 K, trimethylamine was determined by gas chromatographic analysis, which can be explained by the formation and decomposition of trimethylethylammonium ions, (CIl3)3N CH2CH3. 

Korenman et al. [45] studied the solvent-water partition coefficients Ksv/ of ethylamine, n-propylamine, and n-butylamine at 20°C. Based on the data for these amines with a short, linear alkyl chain, the contributions to the logarithm of the solvent-water partition coefficients were found to be constant among particular solvent classes. The contribution values are shown in Table 13.4.1. Accordingly, A log K0VI for CH2 is 0.50. 

Phthalimide. C<,H4 (CO), NH, is an imide of commercial and industrial importance, forming a number of interesting derivatives. With alcoholic potash, phthalimide forms a potassium derivative. C(,H4 (COb -NK. which, when reacted with ethyl iodide (or other alkyl halides), yields eihylphthalimidc. C(,H4 (COi N - C2Hj Ihe latter product, when hydrolyzed wilh an acid or alkali, further yields ethylamine. Such reaction chains are useful in ihe preparation of certain primary amines and their derivatives. 

Sodium cyanide reacts with alkyl bromides by the SN2 mechanism. Reduction of the cyano group with lithium aluminum hydride yields a primary amine. This reveals the structure of mescaline to be 2-(3,4,5-trimethoxyphenyl)ethylamine. 

With two nitrile groups, the delocalized anion is so stable that even a weak, neutral amine (tri-ethylamine) is sufficiently basic to deprotonate the starting material. Here double alkylation again takes place note that the electrophile is good at Sn2, and the solvent is dipolar and aprotic (DMSO and DMF have similar properties). The doubly alkylated quaternary product was formed in 100% yield. 

Triethylamine was obtained in a yield of 16% by alkylating ethylamine drop by drop with acetaldehyde in a 1 2 molar ratio in a colloidal platinum solution at room temperature and 0.1 MPa H2.12 Benzyldiethylamine was prepared in a 31% yield from ethylamine, benzaldehyde, and acetaldehyde in a 1 1 1 molar mixture over a colloidal platinum in H20-AcOH-EtOH at room temperature and 0.3 MPa H2. The yield of the tertiary amine, however, was improved to more than 50% by alkylating ethylbenzy-lamine with acetaldehyde. 

In the course of investigations involving the reaction of lithium triethylhydroborate with conjugated nitroalkenes (61),A -ethylamines (62) were consistently observed as by-products (equation 34). The intermediacy of nitroso compounds has been confirmed in this reaction which provides a useful method for the preparation of A -ethylated amine derivatives. These A -alkylated products are not produced when sterically demanding reagents, such as potassium tri-s-butylborohydride, are used. Apparently, the competition between reduction and alkylation of the nitroso group is sensitive to steric effects. 

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