Propylamine carbonate

Constitutional isomerism is not limited to alkanes—it occurs widely throughout organic chemistry. Constitutional isomers may have different carbon skeletons (as in isobutane and butane), different functional groups (as in ethanol and dimethyl ether), or different locations of a functional group along the chain (as in isopropylamine and propylamine). Regardless of the reason for the isomerism, constitutional isomers are always different compounds with different properties, but with the same formula. 

A synthetically useful virtue of enol triflates is that they are amenable to palladium-catalyzed carbon-carbon bond-forming reactions under mild conditions. When a solution of enol triflate 21 and tetrakis(triphenylphosphine)palladium(o) in benzene is treated with a mixture of terminal alkyne 17, n-propylamine, and cuprous iodide,17 intermediate 22 is formed in 76-84% yield. Although a partial hydrogenation of the alkyne in 22 could conceivably secure the formation of the cis C1-C2 olefin, a chemoselective hydrobora-tion/protonation sequence was found to be a much more reliable and suitable alternative. Thus, sequential hydroboration of the alkyne 22 with dicyclohexylborane, protonolysis, oxidative workup, and hydrolysis of the oxabicyclo[2.2.2]octyl ester protecting group gives dienic carboxylic acid 15 in a yield of 86% from 22. 

APM-3,4-HOPY is a bidentate 3-hydroxy,4-pyridinone featuring a propylamine moiety attached to the pyridine N and a methyl group on carbon 2 of the pyridine ring. sThis value is reported as a lh n-... 

They achieved fast separation of -blockers in less than 2 min on a short column using supercritical carbon dioxide modified with 20% ethanol and small amount of n-propylamine as the mobile phase. 

Direct condensation of propargyl alcohols 125 (Fig. 5.31), carbon dioxide, and propylamine can be realized by Ru3(CO)i2 catalysis at 80 °C under CO2 pressure of 50 kg/cm. The reaction mechanism is rationalized as shown below. When diethylamine is used in place of a primary amine, 2-oxoalkyl WA -diethylcarba-mates are isolated in moderate yields. 

Table II lists first-order rate constants, corrected for hydrolysis of ester in buffer alone. Propylamine served as a reference amine in its presence k (in min-1) for aminolysis decreased progressively from 0.98 x 10-2 to 0.51 x 10-2 to 0.05 x 10-2 as the length of the acyl group increased from 2 to 12 carbons (see Table II). The sharp drop for nitrophenyl laurate may be the result of micelle formation23 even at concentrations of 6x 10-6 M...

Therefore, JCN increases in the series propylamine, N-methylaniline, N-methyl-N-pro-pynylaniline due to increasing s character of carbon hybrid orbitals,... 

The structure of MDA can be viewed as an aromatic ring (the 3,4-methylenedioxyphenyl ring) with a three carbon chain sticking out from it. The amine group is on the second of the three carbon atoms. The isomers, with the amine function moved to the first of these carbons atoms (a benzylamine) and with the amine function moved to the third (furthest out atom) of these carbon atoms (a (n)-propylamine), are known and both have been assayed. 

The (n)-propylamine counterpart (as if one were to move the amine function the other direction, from the beta-carbon to the gamma-carbon of the three carbon chain of the amphetamine molecule) is gamma-3,4-methylenedioxy-phenylpropylamine or 1 -amino-3-(3,4-methylenedioxyphenyl)propane, GAMMA. The hydrochloride salt has a mp of 204-205 °C. At oral levels of 200 milligrams there was some physical ill-at-ease, possible time distortion, and a feeling of being keenly aware of one s surroundings. The duration of effects was 4 hrs. 

Kempter and co-workers prepared benzodiazocines 134 (R = R1 = H R2 = H, Me) from 135 (R = H, Me) by reduction and subsequent cyclo-condensation with the appropriate carbonyl compound (75MI7 87ZC36). For example, these workers condensed 3-(o-aminophenyl)propylamine with either phosgene or alkyl chloroformate to obtain 134 (R = R1 = R2 = H, X = O). Reaction of the same diamine (77MI5 87ZC36) and substituted derivatives (77MI5) with carbon disulfide afforded thio-... 

The proton and carbon NMR spectra of 2,2,3,3,3-pentafluoro-propylamine are given in Figures 6.14 and 6.15. In its proton spectrum, one sees the triplet at 3.22 ppm due to the CH2 group, with its three-bond F-H coupling constant of 15.5 Hz. 

The mixture was then heated to reflux for 3 h, cooled and treated cautiously (vigorous stirring) with water, then with 15% aqueous sodium hydroxide and finally with water. The mixture was stirred for 20 min and filtered. The filtrate was dried over anhydrous potassium carbonate and evaporated. The residue was distilled under water-pump vacuum to give pure 2-(3-methoxy-phenoxy)-propylamine, boiling point 148-152°C/13 mm. 

Essentially, all primary skin irritants include acids, alkalis, metals, salts, and solvents. Among organic acids one may include acetic acid, acrylic acid, carbolic acid, chloroacetic acid, formic acid, lactic acid, oxalic acid, and salicylic acid. Among inorganic acids one may list arsenious acid, chromic acid, hydrochloric acid, hydrofluoric acid, nitric acid, phosphoric acid, and sulfuric acid. Alkalis include butylamines, ethylamines, ethanolamines, methylamines, propylamines, and triethanolamine. One also may include ammonium carbonate, ammonium hydroxide, calcium carbonate, calcium cyanamide, calcium hydroxide, calcium oxide, potassium carbonate, potassium hydroxide, sodium carbonate (soda ash), sodium hydroxide (caustic soda), and sodium silicate. 

A large excess of ammonia suppresses formation of di- and trialkylamines. With a rhodium-on-carbon catalyst in process conditions of 75°C and 50 psig plus continuous removal of ammonia, the reduction of propionitrile with hydrogen proceeds with greater than 85% selectivity for di-n-propylamine, with 2 to 5% mono-n-propylamine coproduct. Several companies produce amines in the C 2 to Ci8 range from fatty nitriles by this route116. 

Magadiite apart from pentasil phases can be found in zeolites synthesized with mono-n-methy1-, -ethyl-, -propyl- or -butylamine, with di-n-methyl-, -ethyl- or -propylamine, with tri-n-methyl- or -ethylamine and with tetramethylammonium iodide. Table IV shows that the zeolite content increases with the number of carbon atoms per group and with the number of alkyl groups. 

Removal of one of the ethylene portions of the piperidine ring leaves the phenyl-propylamine skeleton of the phenyl piperidines. These are the most simplified structures still to have opioid receptor activity. The phenylpropylamines still follow the SAR of morphine on the basis that they possess a basic nitrogen which is two carbons away from a central quaternary carbon atom having a benzene ring attached [18]. In the case of methadone (29 Fig. 11.16) [65], the prototype phenyl-propylamine, the quaternary carbon contains another benzene ring and a propio-nyl moiety. The basic nitrogen is still tertiary with two methyl groups present. 

Cobalt boride catalysts have been shown to be highly active and selective in the hydrogenation of nitriles to primary amines.103,104 Barnett used Co boride (5%) supported on carbon for the hydrogenation of aliphatic nitriles and obtained highest yields of primary amines among the transition metals and metal borides investigated including Raney Co.104 An example with propionitrile, where a 99% yield of propylamine was obtained in the presence of ammonia, is seen in eq. 7.29. 

Ionic and nonionic lipopeptides give microemulsions when an aliphatic alcohol or amine with less than 7 carbon atoms is used as cosurfactant. Nevertheless the best cosurfactants are butanol, propanol, butylamine and propylamine. 

Amides are more conveniently reduced with lithium aluminum hydride in ether solution to yield amines with the same carbon content, e.g, tri-ethylamine from N,N-diethylacetamide (50%) and ethyl-n-propylamine from N-ethylpropionamide (53%). ° The same conversion has been accomplished by an electrolytic reduction. ... 

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