90150-05-3

Usage

Uses

Used in Pharmaceutical Synthesis:
N-(CYCLOHEXYLMETHYL)DIETHYL AMINO is used as a reagent in pharmaceutical synthesis for its ability to facilitate the creation of various medicinal compounds. Its cyclohexyl and diethylamino groups contribute to the formation of complex organic molecules that are integral to drug development.
Used in Organic Chemistry Research:
In the field of organic chemistry research, N-(CYCLOHEXYLMETHYL)DIETHYL AMINO is utilized as a key component in experiments and studies aimed at understanding and advancing chemical reactions and processes. Its presence can influence reaction mechanisms and outcomes, providing valuable insights for researchers.
Used in Chemical Synthesis:
N-(CYCLOHEXYLMETHYL)DIETHYL AMINO is employed as a versatile building block in the synthesis of a wide array of organic compounds. Its unique structure allows it to participate in multiple types of chemical reactions, broadening its applicability in the creation of new materials and substances.
Used in Material Science:
In material science, N-(CYCLOHEXYLMETHYL)DIETHYL AMINO is used as a component in the development of novel materials with specific properties. Its cyclohexyl and diethylamino groups can influence the physical and chemical characteristics of the materials, making it a useful compound in material innovation.
Safety Precautions:
Due to its potential hazards, N-(CYCLOHEXYLMETHYL)DIETHYL AMINO must be handled with care. Proper safety measures should be taken during its use, including the use of personal protective equipment, working in a well-ventilated area, and following established safety protocols for chemical storage and disposal.

Upstream product

• 109-89-7 diethylamine 
• 2550-36-9 Cyclohexylmethyl bromide 
• 5461-52-9 N,N-diethylcyclohexanecarboxamide 
• 13686-66-3 N,N-diethylaminodimethylsilane 
• 2043-61-0 cyclohexanecarbaldehyde 
• 3218-02-8 cyclohexylmethylamine 
• 75-05-8 acetonitrile 
• 124-38-9 carbon dioxide 
• 110-83-8 cyclohexene 
• 100-50-5 3-Cyclohexene-1-carboxaldehyde 
• 64-17-5 ethanol 
• 64847-82-1 cyclohexylmethylene diacetate 

Relevant academic research and scientific papers

Atomically dispersed Rh on hydroxyapatite as an effective catalyst for tandem hydroaminomethylation of olefins

Tandem hydroaminomethylation is an efficient and green route for one-pot synthesis of amines directly from olefins. Herein, heterogeneous hydroxyapatite (HAP) supported single-atom Rh catalyst was prepared and used for tandem hydroaminomethylation of olefins. Characterization techniques confirmed the atomic dispersion of Rh species on HAP. Up to 99% conversion of 1-hexene with high selectivity to the desired amines (93.2%) was obtained over 0.5Rh1/HAP catalyst. Mechanism study demonstrated that the first hydroformylation step during the tandem catalytic process was rate-determining. Compared with the Rh nanoparticles on other oxide supports (Mg3Al, MgO and Al2O3), the atomically dispersed Rh sites on HAP ensured the high hydroformylation activity, thereby guaranteed the outstanding catalytic performance for the total tandem process. Furthermore, various corresponding amines can be obtained with satisfactory yields over 0.5Rh1/HAP catalyst from a wide scope of olefins or amines substrates.

Rhodium-Catalysed Reductive Amination for the Synthesis of Tertiary Amines

A procedure for the synthesis of tertiary amines via reductive amination of aldehydes with molecular hydrogen as a reducing agent using homogeneous rhodium catalysis is presented. Using an amine to aldehyde ratio of 4/1 enabled the synthesis of tertiary amines from nine different aldehydes and nine different secondary amines with selectivities up to 99% and turnover frequencies (TOF) up to 7200 h?1. The reaction showed a high tolerance against alcohol and ester functions allowing the formation of multifunctional molecules. In addition, secondary amines can also be produced by this synthesis. For all compounds, activities were determined by hydrogen gas-uptake. In order to increase the sustainability and efficiency of the procedure, a dosing strategy has been successfully developed. Using the determined reaction indicators enabled the stoichiometric use of aldehydes and amines without significant loss of selectivity. (Figure presented.).

NEW METHOD FOR THE SYNTHESIS OF UNSYMMETRICAL TERTIARY AMINES

Disclosed is a new method for the synthesis of unsymmetrical tertiary amines using alcohol and an imine, and to new tertiary amines.

Carbon dioxide transformation in imidazolium salts: Hydroaminomethylation catalyzed by Ru-complexes

The catalytic species generated by dissolving Ru3(CO)12 in the ionic liquids 1-n-butyl-3-methyl-imidazolium chloride or 1-n-butyl-2,3-dimethyl-imidazolium chloride are efficient multifunctional catalysts for: (a) reverse water-gas shift, (b) hydroformylation of alkenes, and (c) reductive amination of aldehydes. Thus the reaction of alkenes with primary or secondary amines (alkene/amine, 1:1) under CO2/H2 (1:1) affords the hydroamino-methylations products in high alkene conversions (up to 99%) and selectivities (up to 96%). The reaction proceeds under relatively mild reaction conditions (120 °C, 60 bar = 6 MPa) and affords selectively secondary and tertiary amines. The presence of amine strongly reduces the alkene hydrogenation competitive pathway usually observed in the hydroformylation of terminal alkenes by Ru complexes. The catalytic system is also highly active for the reductive amination of aldehydes and ketones yielding amines in high yields (> 90%).

Controlled Reduction of Tertiary Amides to the Corresponding Alcohols, Aldehydes, or Amines Using Dialkylboranes and Aminoborohydride Reagents

Dialkylboranes and aminoborohydrides are mild, selective reducing agents complementary to the commonly utilized amide reducing agents, such as lithium aluminum hydride (LiAlH4) and diisobutylaluminum hydride (DIBAL) reagents. Tertiary amides were reduced using 1 or 2 equiv of various dialkylboranes. The reduction of tertiary amides required 2 equiv of 9-borabicyclo[3.3.1]nonane (9-BBN) for complete reduction to give the corresponding tertiary amines. One equivalent of sterically hindered disiamylborane reacts with tertiary amides to afford the corresponding aldehydes. Aminoborohydrides are powerful and selective reducing agents for the reduction of tertiary amides. Lithium dimethylaminoborohydride and lithium diisopropylaminoborohydride are prepared from n-butyllithium and the corresponding amine-borane. Chloromagnesium dimethylaminoborohydride (ClMg+[H3B-NMe2]-, MgAB) is prepared by the reaction of dimethylamine-borane with methylmagnesium chloride. Solutions of aminoborohydride reduce aliphatic, aromatic, and heteroaromatic tertiary amides to give the corresponding alcohol, amine, or aldehyde depending on the steric requirement of the tertiary amide and the aminoborohydride used.

Selective N-alkylation of amines using nitriles under hydrogenation conditions: Facile synthesis of secondary and tertiary amines

Nitriles were found to be highly effective alkylating reagents for the selective N-alkylation of amines under catalytic hydrogenation conditions. For the aromatic primary amines, the corresponding secondary amines were selectively obtained under Pd/C-catalyzed hydrogenation conditions. Although the use of electron poor aromatic amines or bulky nitriles showed a lower reactivity toward the reductive alkylation, the addition of NH4OAc enhanced the reactivity to give secondary aromatic amines in good to excellent yields. Under the same reaction conditions, aromatic nitro compounds instead of the aromatic primary amines could be directly transformed into secondary amines via a domino reaction involving the one-pot hydrogenation of the nitro group and the reductive alkylation of the amines. While aliphatic amines were effectively converted to the corresponding tertiary amines under Pd/C-catalyzed conditions, Rh/C was a highly effective catalyst for the N-monoalkylation of aliphatic primary amines without over-alkylation to the tertiary amines. Furthermore, the combination of the Rh/C-catalyzed N-monoalkylation of the aliphatic primary amines and additional Pd/C-catalyzed alkylation of the resulting secondary aliphatic amines could selectively prepare aliphatic tertiary amines possessing three different alkyl groups. According to the mechanistic studies, it seems reasonable to conclude that nitriles were reduced to aldimines before the nucleophilic attack of the amine during the first step of the reaction.

Lewis acid-catalyzed reductive amination of carbonyl compounds with aminohydrosilanes

The TiCl4-catalyzed reaction of aromatic carbonyl compounds with (dialkylamino)dimethylsilanes gave tertiary amines in moderate to high yields. The reductive amination of aliphatic aldehydes was effectively catalyzed by ZnI2. Methyl

Controlled reduction of tertiary amides to the corresponding aldehydes or amines using dialkylboranes

Several tertiary amides were reduced using one or two equivalents of various dialkylboranes, such as 9-borabicyclo[3.3.1] nonane (9-BBN), dicyclohexylborane (Chx2BH), or disiamylborane (Sia2BH). The reduction of tertiary amides having alkyl substituents of varying steric requirement at the nitrogen atom, required two equivalents of 9-BBN for complete reduction and gave the corresponding tertiary amines. However, sterically more hindered dialkylboranes such as Chx2BH and Sia2BH, reacted in 1:1 stoichiometry with tertiary amides and partially reduced them to the corresponding aldehydes.

Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures

Sodium triacetoxyborohydride is presented as a general reducing agent for the reductive amination of aldehydes and ketones. Procedures for using this mild and selective reagent have been developed for a wide variety of substrates. The scope of the reaction includes aliphatic acyclic and cyclic ketones, aliphatic and aromatic aldehydes, and primary and secondary amines including a variety of weakly basic and nonbasic amines. Limitations include reactions with aromatic and unsaturated ketones and some sterically hindered ketones and amines. 1,2-Dichloroethane (DCE) is the preferred reaction solvent, but reactions can also be carried out in tetrahydrofuran (THF) and occasionally in acetonitrile. Acetic acid may be used as catalyst with ketone reactions, but it is generally not needed with aldehydes. The procedure is carried out effectively in the presence of acid sensitive functional groups such as acetals and ketals; it can also be carried out in the presence of reducible functional groups such as C-C multiple bonds and cyano and nitro groups. Reactions are generally faster in DCE than in THF, and in both solvents, reactions are faster in the presence of AcOH. In comparison with other reductive amination procedures such as NaBH3CN/MeOH, borane-pyridine, and catalytic hydrogenation, NaBH(OAc)3 gave consistently higher yields and fewer side products. In the reductive amination of some aldehydes with primary amines where dialkylation is a problem we adopted a stepwise procedure involving imine formation in MeOH followed by reduction with NaBH4.

Aminoborohydrides as Reducing Agents. 1. Sodium (Dimethylamino)- and (tert-Butylamino)borohydrides as Selective Reducing Agents

Replacement of a hydride in borohydride by an electron-donating alkylamino group greatly enhances the reducing ability of the resulting reagents.Thus, sodium (dimethylamino)- and (tert-butylamino)borohydrides (1, NaDMAB, and 2, NaTBAB, respectively) not only reduce aldehydes and ketones to alcohols but also are effective for the conversion of esters to alcohols and primary amides to amines in good to excellent yields.Tertiary amides are reduced to alcohols (i.e., N,N-dimethylamides) or amines (i.e.N,N-diisopropylamides) depending on the steric bulk of the alkyl substituents on nitrogen.However, secondary amides are not reduced by the reagents allowing selective conversion of primary and tertiary amides in the presence of secondary amides.Nitriles are attacked by the reagents but do not afford synthetically useful amounts of amine products.Aryl halides are slowly converted to arenes, but alkyl halides and epoxides undergo unusual reactions with the amino portion of the reagents.