5779-51-1

Usage

InChI:InChI=1/C16H27N/c1-3-5-13-17(14-6-4-2)15-12-16-10-8-7-9-11-16/h7-11H,3-6,12-15H2,1-2H3

Upstream product

• 100-42-5 styrene 
• 111-92-2 dibutylamine 
• 103-63-9 1-phenyl-2-bromoethane 
• 123-72-8 butyraldehyde 
• 64-04-0 phenethylamine 
• 71-36-3 butan-1-ol 
• 109-65-9 1-bromo-butane 
• 23068-45-3 N-Butyl-2-phenylethylamine 
• 536-74-3 phenylacetylene 
• 140-29-4 phenylacetonitrile 
• 122-78-1 phenylacetaldehyde 

Relevant academic research and scientific papers

Ambient Moisture Accelerates Hydroamination Reactions of Vinylarenes with Alkali-Metal Amides under Air

A straightforward alkali-metal-mediated hydroamination of styrenes using biorenewable 2-methyltetrahydrofuran as a solvent is reported. Refuting the conventional wisdom of the incompatibility of organolithium reagents with air and moisture, shown here is that the presence of moisture is key in favoring formation of the target phenethylamines over competing olefin polymerization products. The method is also compatible with sodium amides, with the latter showing excellent promise as highly efficient catalysts under inert atmosphere conditions.

Hydroamination of terminal alkynes with secondary amines catalyzed by copper: Regioselective access to amines

A simple and convenient copper-catalyzed hydroamination of arylacetylenes with secondary amines has been performed giving a simple access to aliphatic amines after reduction of the hydroaminated products (E-enamines). Here we described a mild catalytic system utilizing CuCN precatalyst without any additive ligands in a solvent-free system.

Catalytic reductive alkylation of secondary amine with aldehyde and silane by an iridium compound

(Chemical Equation Presented) An efficient methodology for the reductive alkylation of secondary amine with aldehyde and Et3SiH using an iridium complex as a catalyst has been developed. For example, treatment of dibutylamine with butyraldehyde and Et3SiH (a 1:1:1 molar amount of amine, aldehyde, and silane) in 1,4-dioxane at 75°C under the influence of a catalytic amount of [IrCl(cod)]2 gave tributylamine in quantitative yield. In this reaction, no reduction of aldehyde took place. It was found that IrCl3, which is a starting material for preparation of iridium complexes such as [IrCl(cod)]2, acts as an efficient catalyst for the present reductive alkylation of amine. In addition, a cheaper, easy-to-handle, and environmentally friendly reducing reagent such as polymethylhydrosiloxane (PMHS) in place of Et3SiH was also useful. Thus, a variety of secondary amines could be alkylated by allowing them to react with aldehydes and PMHS in the presence of an iridium catalyst to afford the corresponding tertiary amines in good to excellent yields. From the deuterium label experiments, it was revealed that silane and water, generated during the formation of enamine by the reaction of amine and aldehyde, seem to behave as a hydrogen source. The catalytic cycle was discussed.

Cesium effect: High chemoselectivity in direct N-alkylation of amines

A novel method for the mono-N-alkylation of primary amines, diamines, and polyamines was developed using cesium bases in order to prepare secondary amines efficiently. A cesium base not only promoted alkylation of primary amines but also suppressed overalkylations of the produced secondary amines. Various amines, alkyl bromides, and alkyl sulfonates were examined, and the results demonstrated this methodology was highly chemoselective to favor mono-N-alkylation over dialkylation. In particular, use of either sterically demanding substrates or amino acid derivatives afforded the secondary amines exclusively, offering wide applications in peptidomimetic syntheses.

Cesium Hydroxide Promoted Chemoselective N-Alkylation for the Generally Efficient Synthesis of Secondary Amines

(Matrix presented) Selective N-alkylation of primary amines was developed using cesium hydroxide to prepare various secondary amines efficiently. A cesium base not only promoted monoalkylations of primary amines but also suppressed overalkylations. Various amines and alkyl bromides were examined, and the preliminary results demonstrated this methodology was highly chemoselective, favoring mono-N-alkylation over dialkylation. In particular, use of amino acid derivatives afforded the desired secondary amines exclusively.