Hexylamines

Phenyl-3-oxopropanoic acid (25 mmol) and EtjN (87.5 mmol) were dissolved in THF (150 ml) and cooled to —40°C. Ethyl chloroformate (27.5 mmol) was added dropwise to this solution and then the reaction mixture was stirred for 30 min at —20°C. Di-n-hexylamine (27.5 mmol) was added to the suspension and it was stirred at room temperature for an additional hour. The reaction mixture was diluted with water (100 ml) and extracted with ether (400 ml). The extract was washed with aq. 5% HCl (100 ml) and brine (2 X 100 ml) and dried over NajSO. The crude amide was obtained by removal of the solvent in vacuo and phenylhydrazine (25 mmol) was added. The mixture was heated to 100°C for 30 min. The residue was held in vacuo to remove the water formed and then powdered ZnCl2 (125 mmol) was added. The mixture was heated at 170"C with manual stirring for 5 min. The cooled residue was dissolved in acetone (100 ml) and diluted with ether (500 ml). Water (100 ml) was added. The organic layer was separated and washed successively with 5% aq. HCl (100 ml) and brine (2 x 100 ml) and dried over NajSO. The solvent was removed in vacuo, and the residue was recrystallized from EtOAc-hexane. The yield was 79%. 

Compare the calcu lated charge on nitrogen in cycio hexylamine and aniline on Learning By Modeling... 

M-Hexyl alcohol has been prepared by the reduction of ethyl caproate by means of sodium and absolute alcohoB alone or in anhydrous ammonia solution by the reduction of -caproamide by means of sodium and absolute alcohol by the reduction of -caproaldehyde by means of sodium amalgam in dilute sulfuric acid and by means of living yeast, It has also been produced by the action of nitrous acid upon w-hexylamine by the action of sodium upon a mixture of ethyl alcohol and M-butyl alcohol ... 

Diamines formed upon photolysis of 6-quinolyl azide in isopropyl-, n-butyl-, and n-hexylamines are very unstable, so they were cyclized to the corresponding 1-substituted imidazo[4,5-/]quinolines by heating the residue obtained after evaporation of the photolysis solvent with formic acid at reflux (82JCS(P 1)421). Instead... 

Therapeutic Function Nasal decongestant Chemical Name 4-methvl-2-hexylamine carbonate Common Name —... 

Ethyl hexylamine Hexetidine Ethyl glycinate HCI Caroxazone... 

Dicyclohexylammonium nitrite s (DCHN) has a solubility of 3-9g in 100 g of aqueous solution at 25°C, giving a solution pH of about 6-8. Its vapour pressure at 25°C appears to be about 1-3 x 10 N/m but the value for commercial materials depends markedly on purity. It may attack lead, magnesium, copper and their alloys and may discolour some dyes and plastics. Cyclohexylammonium cyclohexyl carbamate (the reaction product of cyclohexylamine and carbon dioxide, usually described as cyclo-hexylamine carbonate or CHC)" is much more volatile than DCHN (vapour pressure 53 N/m at 25°C), and much more soluble in water (55 g in 100cm of solution at 25°C, giving a pH of 10-2). It may attack magnesium, copper, and their alloys, discolour plastics, and attack nitrocellulose and cork. It is said to protect cast iron better than DCHN, and to protect rather better in the presence of moderate concentrations of aggressive salts. 

Properties of PS-A and PS-B (Shimomura, 1991b Shimomura et al., 1993b). Both PS-A and PS-B are colorless viscous liquid, and their absorption spectra resemble that of panal (Fig. 9.6). By NMR analysis and mass spectrometry, PS-A and PS-B are found to be 1-O-decanoylpanal and 1-O-dodecanoylpanal, respectively. As a minor component, 1-O-tetradecanoylpanal has also been isolated. PS-A and PS-B gain chemiluminescence activity when treated with the salt of primary amines (see below for the conditions). Taking the activity obtained with methylamine as 100%, the activities obtained with other amines were ethylamine, 38% ethanolamine, 10% propylamine, 20% hexylamine, 3% and decylamine, 1%. 

Treatment of the precursors with decylamine resulted in a high level of chemiluminescence activity. Taking the activity obtained with decylamine as 100%, the activities obtained with other amines were methylamine, 5% hexylamine, 23% octylamine, 39% and dode-cylamine, 55%. For comparison, the Panellus precursors, PS-A and PS-B, are best activated with methylamine, and a synthetic model compound, K-l, is best activated with hexylamine. 

The procedure is illustrative of a general method of ethylating amines, wherein one reacts the amine with ethylene using an alkali-metal salt of the amine as catalyst.2 Di- -butylamine and -hexylamine have been thus ethylated at 130-160°, aniline, o-toluidine, and N-methylaniline at 240-275°. In general, higher olefins add to amines only sluggishly.2... 

Ethylene carbonate, reaction with potassium thiocyanate, 42, 59 Ethylene sulfide, 42, S9 Ethyl formate, reaction with cyclo-hexylamine, 41, 14 Ethyl- -hexylamine, 43, 47 5-(2-Ethylhexyl)-l,2,3,4,5-pentachloro-cyclopentadiene, 43, 93 Ethylhydrazinium hydrogen oxalate,... 

DMAc. See Dimethylacetamide (DMAc) DMCHA. See V,lV-Dimethylcyclo-hexylamine (DMCHA)... 

OS 8[ [R 25] [P 6] The acylation of acetic anhydride with various amines was investigated all yields ranged from 75 to 100% with the exception of one value of 46% [83]. The lowest yield was obtained for 1-naphfhylamine and the highest for 1-hexylamine. Throughputs were from 3.8 to 68.3 g... 

Methylamine Ethylamine n-Propylamine Mo-Propylamine n-Butylamine. iso-Butylamiiie ec. -B utylamiiie n-Amylamine. i o-Amylamino n-Hexylamine. n-Heptylamine... 

These differences have been identified for two main classes of interactions, namely intramolecular H-bonding and charge delocalization. It has, for instance, been shown for VV-(p-methylbenzyl)hexylamine in water-DCE that its diff (log is 4.51, which is... 

The Buchwald-Hartwig amination reaction has gained great interest in the last decade in both academic and industrial environments. In the work presented herein, we discuss a very interesting effect in the competitive reaction of two amines (benzophenone hydrazone and n-hexylamine) with 3-bromobenzotrifluoride. 

The reactions involving either benzophenone hydrazone or w-hexylamine have been studied by reaction calorimetry. The benzophenone hydrazone reaction presents zero order kinetics, while the hexylamine reaction is first order in the aryl halide and zero order in the amine. Under synthetically relevant conditions, at 90°C, the rate of the hexylamine reaction is about 30-fold higher than the rate of the benzophenone reaction. 

Figure 26.1 represents the heat profile of the benzophenone hydrazone and hexylamine reactions. At the same conditions, at 90°C, the reaction involving hexylamine is considerably faster. The heat profile of the hexylamine reaction at 70°C shows how the reaction has positive order kinetics, while the benzophenone reaction shows overall zero order kinetics. 

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