5830-30-8

Usage

Uses

N,N-Dimethylhexanamide is used as a pharmaceutical intermediate.

InChI:InChI=1/C8H17NO/c1-4-5-6-7-8(10)9(2)3/h4-7H2,1-3H3

Upstream product

• 142-61-0 Hexanoyl chloride 
• 68-12-2 N,N-dimethyl-formamide 
• 506-59-2 N,N-dimethylammonium chloride 
• 74-94-2 dimethylamine borane 
• 142-62-1 hexanoic acid 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 109-67-1 1-penten 
• 127-19-5 N,N-dimethyl acetamide 
• 71-36-3 butan-1-ol 
• 106-70-7 methyl hexanoate 
• 1608-26-0 Hexamethylphosphorous triamide 
• 22809-42-3 6-bromohexanoic acid dimethylamide 
• 82859-40-3 tris(dimethylamino)diiodophosphorane 
• 815-62-3 N,N,N',N'-tetramethylethylendiamine 

Downstream Products

• 58016-28-7 methyl 2,6-dihydroxy-6-pentylbenzoate 
• 4385-04-0 N,N-dimethylhexylamine 
• 66-25-1 hexanal 
• 111-27-3 hexan-1-ol 
• 6683-94-9 1-Phenyl-2-heptanone 
• 102-04-5 1,3-Diphenylpropanone 
• 142-61-0 Hexanoyl chloride 
• 2876-61-1 1-(naphthalen-1-yl)hexan-1-one 
• 52375-87-8 1-(3,4-dimethoxyphenyl)-1-hexanone 
• 1551-14-0 2-hexylpyrrole 
• 89789-81-1 (4-Benzyloxycarbonylamino-decyl)-carbamic acid benzyl ester 

Relevant academic research and scientific papers

Palladium-Catalyzed Aminocarbonylation of Aliphatic Alkenes with N,N-Dimethylformamide as an in Situ Source of CO

The palladium-catalyzed aminocarbonylation of aliphatic alkenes is presented for the first time without the need for external CO pressure. N,N-dimethylformamide (DMF) is used as an in situ source of both the required carbon monoxide and the amine substrate. The applied palladium catalytic system is well-known for a number of carbonylation reactions, including those with CO surrogates and tandem isomerizing carbonylations. The reaction pathway was investigated and proved to proceed by an acid-catalyzed DMF decomposition to CO and dimethyl amine with subsequent aminocarbonylation of the alkene. Pressure-versus-time curves gave more insight into the correlation between acid concentration and aminocarbonylation activity. Aliphatic alkenes (terminal and internal) are transformed, also in commercial glassware, into the corresponding linear N,N-dimethylamides with excellent selectivities. Hence, amide synthesis by aminocarbonylation moves closer to application in standard organic laboratories. Do-it-yourself CO production: The aminocarbonylation of alkenes for aliphatic amide synthesis is presented for the first time using N,N-dimethylamine as an in situ source of both, the required CO and dimethylamine. Excellent selectivities to the linear product are ensured by isomerizing carbonylation applying a [Pd]/1,2-DTBPMB system. 1,2-DTBPMB=1,2-bis((di-tert-butylphos- phino)methyl)benzene.

Deoxygenative hydroboration of primary, secondary, and tertiary amides: Catalyst-free synthesis of various substituted amines

Transformation of relatively less reactive functional groups under catalyst-free conditions is an interesting aspect and requires a typical protocol. Herein, we report the synthesis of various primary, secondary, and tertiary amines through hydroboration of amides using pinacolborane under catalyst-free and solvent-free conditions. The deoxygenative hydroboration of primary and secondary amides proceeded with excellent conversions. The comparatively less reactive tertiary amides were also converted to the corresponding N,N-diamines in moderate yields under catalyst-free conditions, although alcohols were obtained as a minor product.

Amine-boranes as Dual-Purpose Reagents for Direct Amidation of Carboxylic Acids

Amine-boranes serve as dual-purpose reagents for direct amidation, activating aliphatic and aromatic carboxylic acids and, subsequently, delivering amines to provide the corresponding amides in up to 99% yields. Delivery of gaseous or low-boiling amines as their borane complexes provides a major advantage over existing methodologies. Utilizing amine-boranes containing borane incompatible functionalities allows for the preparation of functionalized amides. An intermolecular mechanism proceeding through a triacyloxyborane-amine complex is proposed.

Catalytic Enantioselective α-Fluorination of 2-Acyl Imidazoles via Iridium Complexes

The first highly enantioselective α-fluorination of 2-acyl imidazoles utilizing iridium catalysis has been accomplished. This transformation features mild conditions and a remarkably broad substrate scope, providing an efficient and highly enantioselective approach to obtain a wide range of fluorine-containing 2-acyl imidazoles which are found in a variety of bioactive compounds and prodrugs. A large scale synthesis has also been tested to demonstrate the potential utility of this fluorination method.

A highly efficient catalytic α-alkylation of unactivated amides using primary alcohols

The α-alkylation of unactivated amides with alcohols is described. Using a NCP-type pincer Ir complex as the precatalyst and KOtBu as the base, the reactions of secondary or tertiary acetamides with benzyl or nonbenzyl primary alcohols occur at 80 °C, furnishing the alkylation products in good yields. This method represents a practical and green means of α-alkylation of amides in a relatively mild, efficient, and selective manner with low catalyst loadings (0.5 mol %).

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.

Iridium-catalyzed selective α-alkylation of unactivated amides with primary alcohols

The first α-alkylation of unactivated amides with primary alcohols is described. An effective and robust iridium pincer complex has been developed for selective α-alkylation of tertiary and secondary acetamides involving a borrowing hydrogen methodology. The method is compatible with alcohols bearing various functional groups. This presents a convenient and environmentally benign protocol for α-alkylation of amides.

Cyclopropylamines from N,N-dialkylcarboxamides and grignard reagents in the presence of titanium tetraisopropoxide or methyltitanium triisopropoxide

Thirty-three different N,N-dialkyl- and N-alkyl-N-phosphorylalkyl- substituted carboxamides 9-17 were treated with unsubstituted as well as with 2-alkyl-, 2,2-dialkyl-, and 3-alkenyl-substituted ethylmagnesium bromides 6 in the presence of stoichiometric amounts of titanium tetraisopropoxide or methyltitanium triisopropoxide to furnish substituted cyclopropylamines 20-25 in 20-98 % yield, depending on the substituents with no (1:1) to excellent (>25:1) diastereoselectivities. Generally higher yields (up to 98 %) of the cyclopropylamines 20-28 without loss of the diastereoselectivity were obtained with methyltitanium triisopropoxide as the titanium mediator. Under these conditions, even dioxolane-protected ketones and halogen-substituted and chiral as well as achiral alkyloxyalkyl-substituted carboxamides could be converted to the correspondingly substituted cyclopropylamines with unsubstituted as well as phenyl- and a variety of alkyl-substituted ethylmagnesium bromides in addition to numerous heteroatom-containing (e.g., halogen-, trityloxy-, tetrahydropyranyloxy-substituted) Grignard reagents (62 examples altogether). The transformation of N,N-diformylalkylamines 54 with ethylmagnesium bromide in the presence of methyltitanium triisopropoxide to N,N-dicyclopropyl-N- alkylamines 55 can be brought about in up to 82 % yield (6 examples). An asymmetric variant of the titanium-mediated cyclopropanation of N,N-dialkylcarboxamides has been developed by applying chiral titanium mediators generated from stoichiometric amounts of titanium tetraisopropoxide and chiral diamino or diol ligands, respectively. The most efficient chiral mediators turned out to be titanium bistaddolates that provided the corresponding cyclopropylamines with enantiomeric excesses (ee) of up to 84 %. Evaluation of several silyl-based additives revealed that the reaction can also efficiently be carried out with substoichiometric amounts (down to 25 Mol %) of the titanium reagent, as long as 2-aryl- or 2-ethenyl-substituted ethylmagnesium halides are used and a concomitant slight decrease in yields is accepted. The newly developed methodology was successfully applied for the preparation of analogues with cyclopropylamine moieties of known drugs and natural products such as the nicotine metabolite (S)-Cotinine as well as the insecticides Dinotefuran and Imidacloprid. Ti is it: Cyclopropylamines have been obtained in low to excellent yield through the reaction of different N,N-dialkyl- and N-alkyl-N- phosphorylalkyl-substituted carboxamides with Grignard reagents in the presence of stoichiometric amounts of titanium tetraisopropoxide or methyltitanium triisopropoxide (see scheme). Copyright

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.

Some features of an SmI2-(Me2N)3P-THF system. Transformation of esters into dimethylamides

Sm11-intermediates generated upon addition of (Me2N)3P to a solution of SmI2 in THF exhibit the properties of a single-electron reducing agent and an N-nucleophile. In particular, N,N-dimethylamides are formed from esters.