1118-92-9

Usage

Chemical Properties

colourless liquid

InChI:InChI=1/C10H21NO/c1-4-5-6-7-8-9-10(12)11(2)3/h4-9H2,1-3H3

Upstream product

• 124-07-2 Octanoic acid 
• 124-40-3 dimethyl amine 
• 111-25-1 1-bromo-hexane 
• 127-19-5 N,N-dimethyl acetamide 
• 68-12-2 N,N-dimethyl-formamide 
• 111-64-8 n-octanoic acid chloride 
• 111-27-3 hexan-1-ol 
• 7378-99-6 N,N-dimethyloctanamide 
• 592-41-6 1-hexene 
• 62384-04-7 (methylthio)acetyl N,N-dimethylamide 

Downstream Products

• 7378-99-6 N,N-dimethyloctanamide 
• 111-86-4 n-Octylamine 
• 111-65-9 octane 
• 111-87-5 octanol 
• 124-07-2 Octanoic acid 
• 124-40-3 dimethyl amine 
• 3007-71-4 N-octylaniline 
• 78510-02-8 <1-²H2>-1-octanol 

Relevant academic research and scientific papers

N,N-dimethylamination of acid chlorides with DMF

A solution of acid chlorides 3a-g in DMF solvent was refluxed to give N,N-dimethylamides 4a-f and 5g in excellent yields.

Ruthenium hydride/nitrogen tridentate ligand-catalyzed α-alkylation of acetamides with primary alcohols

The α-alkylation reaction of acetamides with primary alcohols to afford the corresponding amides was accomplished effectively using RuHCl(CO)(PPh3)3 as a catalyst, nitrogen tridentate ligand L1 as an additive, and KOtBu as a base. While the addition of bpy was effective only for benzylic alcohols, L1 affected the alkylation reaction when both benzylic and non-benzylic type alcohols were used.

METHOD FOR PRODUCING AMIDE COMPOUND

PROBLEM TO BE SOLVED: To provide a method whereby, while using a catalyst that contains a transition metal and can be relatively easily synthesized, even with a small amount of the transition metal, an amide compound can be produce efficiently by the α-alkylation of the amide compound. SOLUTION: A method for producing an amide compound includes the step of: causing a primary alcohol compound and an amide compound to react with each other in a reaction liquid containing a transition metal nanoparticle (M-NPs) of at least one of a ruthenium nanoparticle or an iridium nanoparticle, and a base, to produce an amide compound. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT

Manganese-catalyzed direct C-C coupling of α-C-H bonds of amides and esters with alcohols: Via hydrogen autotransfer

Herein we report an efficient manganese-catalyzed C-alkylation of unactivated amides and tert-butyl acetate using alcohols as alkylating agents. This elegant approach exhibits a broad substrate scope providing the C-C coupled products of amides via a hydrogen auto-transfer strategy using aryl, heteroaryl, and aliphatic alcohols.

Sustainable Alkylation of Unactivated Esters and Amides with Alcohols Enabled by Manganese Catalysis

The first example of manganese-catalyzed C-alkylation of the carboxylic acid derivatives is reported. The bench-stable homogeneous manganese complex enables the transformation of the renewable alcohol and carboxylic acid derivative feedstock to higher value esters and amides. The reaction operates via hydrogen autotransfer and ideally produces water as the only side product. Importantly, aliphatic-, benzylic-, and heterocyclic-containing alcohols can be used as alkylating reagents, eliminating the need for mutagenic alkyl halides.

Supported Gold Nanoparticles for Efficient α-Oxygenation of Secondary and Tertiary Amines into Amides

Although the α-oxygenation of amines is a highly attractive method for the synthesis of amides, efficient catalysts suited to a wide range of secondary and tertiary alkyl amines using O2as the terminal oxidant have no precedent. This report describes a novel, green α-oxygenation of a wide range of linear and cyclic secondary and tertiary amines mediated by gold nanoparticles supported on alumina (Au/Al2O3). The observed catalysis was truly heterogeneous, and the catalyst could be reused. The present α-oxygenation utilizes O2as the terminal oxidant and water as the oxygen atom source of amides. The method generates water as the only theoretical by-product, which highlights the environmentally benign nature of the present reaction. Additionally, the present α-oxygenation provides a convenient method for the synthesis of18O-labeled amides using H218O as the oxygen source.

General and Mild Cobalt-Catalyzed C-Alkylation of Unactivated Amides and Esters with Alcohols

The borrowing hydrogen or hydrogen autotransfer methodology is an elegant and sustainable or green concept to construct carbon-carbon bonds. In this concept, alcohols, which can be obtained from barely used and indigestible biomass, such as lignocellulose, are employed as alkylating reagents. An especially challenging alkylation is that of unactivated esters and amides. Only noble metal catalysts based on iridium and ruthenium have been used to accomplish these reactions. Herein, we report on the first base metal-catalyzed α-alkylation of unactivated amides and esters by alcohols. Cobalt complexes stabilized with pincer ligands, recently developed in our laboratory, catalyze these reactions very efficiently. The precatalysts can be synthesized easily from commercially available starting materials on a multigram scale and are self-activating under the basic reaction conditions. This Co catalyst class is also able to mediate alkylation reactions of both esters and amides. In addition, we apply the methodology to synthesize ketones and to convert alcohols into aldehydes elongated by two carbon atoms.

Ruthenium-catalyzed direct α-alkylation of amides using alcohols

The highly efficient direct α-alkylation of unactivated amides has been accomplished using alcohols in the presence of the Ru-PNN catalyst (0.1 mol%) with a high turnover number. Using this approach, 2-oxindole was directly transformed into C3-alkylated 3-hydroxyindolin-2-one in one step without the use of any oxidant.

Copper-catalyzed amide bond formation from formamides and carboxylic acids

A highly efficient copper-catalyzed approach to form amide bonds from formamides and carboxylic acids was developed. This protocol shows broad substrate scopes and high yields in the presence of 1 mol% catalyst and 4.0 equiv. formamides.

PROCESS FOR PRODUCING N,N-DIALKYL SUBSTITUTED FATTY ACIDS AMIDES

Disclosed herein is a process for producing Dialkyl substituted fatty acids amides. More particularly the present invention provides a process for producing pure form of N,N-dimethylamide of aliphatic carboxylic acids, wherein the aliphatic carboxylic acid is Octanoic Acid and Hexanoic Acid. The disclosed process comprises condensing Alkanoyl Chloride with dilute solution of Dialkylamine at a temperature of about 8 to 12°C and isolating the crude by salting out the reaction mixture employing Sodium Chloride and distilling the same under vacuum.