5531-33-9

Usage

Uses

N-(2-Methyl-1-phenylpropan-2-yl)acetamide is a byproduct from the preparation of benzolactams by palladium-catalyzed carbonylation of arylethylamines and α-amino benzenepropanoates.

InChI:InChI=1/C12H17NO/c1-10(14)13-12(2,3)9-11-7-5-4-6-8-11/h4-8H,9H2,1-3H3,(H,13,14)

Upstream product

• 100-86-7 2-Methyl-1-phenyl-2-propanol 
• 75-05-8 acetonitrile 
• 6921-34-2 benzylmagnesium chloride 
• 201230-82-2 carbon monoxide 
• 64-19-7 acetic acid 
• 122-09-8 Phentermin 
• 5669-14-7 2,2-dimethyl-3-phenylpropanoic acid 
• 2206-26-0 [D₃]acetonitrile 
• 538-93-2 1-phenyl-2-methylpropane 

Downstream Products

• 1197-21-3 phentermine hydrochloride 
• 122-09-8 Phentermin 
• 5531-43-1 N-Aethyl-N-(1,1-dimethyl-phenaethyl)-amin 
• 55281-81-7 2,4,4-trimethyl-5-phenyl-4,5-dihydro-oxazole 
• 76613-27-9 N,N'-bis(1,1-dimethyl-2-phenylethyl)thiadiaziridine 1,1-dioxide 
• 76613-21-3 N,N'-bis(1,1-dimethyl-2-phenylethyl)sulfamide 
• 26307-22-2 N,N'-bis(2-methyl-3-phenyl-2-propyl)diazene 
• 55281-79-3 N-chloro-N-(1,1-dimethyl-2-phenyl-ethyl)-acetamide 

Relevant academic research and scientific papers

Hypervalent Iodine(III)-Mediated Decarboxylative Ritter-Type Amination Leading to the Production of α-Tertiary Amine Derivatives

α-Tertiary amines (ATAs) are attractive structural motifs that are frequently found in biologically active molecules. Therefore, the development of an efficient method for the synthesis of ATAs represents an important research topic in the field of medicinal chemistry as well as organic chemistry. Although the Ritter reaction is a reliable approach for preparing α-tertiary amine derivatives via intermolecular amination reactions, the typical methods suffer from disadvantages such as harsh reaction conditions and the use of strong acids. Because of this, it has been of limited use in the synthesis of ATAs. We report here on the decarboxylative Ritter-type amination of carboxylic acids bearing an α-quaternary carbon center using a combination of PhI(OAc)2 and molecular iodine (I2) to produce the corresponding α-tertiary amine derivatives. This reaction proceeded at ambient temperature on the benchtop with a fluorescent light. Mechanistic investigations suggest that the reaction proceeds via the formation of an alkyl iodide and a higher oxidation state iodine(III) species as key intermediates. Similarly, a stepwise protocol for the Ritter-type amination of alcohols via the formation of oxalic acid monoalkyl esters was also achieved. The present methods represent a useful tool for the synthesis of ATAs that are difficult to prepare by conventional methods.

Mechanochemical ritter reaction: A rapid approach to functionalized amides at room temperature

A fast and efficient mechanochemical Ritter reaction between alcohols and nitriles under mild conditions is demonstrated. The reaction proceeds rapidly at room temperature in a solvent-free or low-solvent environment by using a Br?nsted acid catalyst. Its general application has been verified through a substrate screening comprising a wide range of functionalized nitriles as well as secondary and tertiary alcohols. Gentle Ritter: A fast and efficient mechanochemical Ritter reaction under mild conditions is described. The reaction proceeds rapidly at room temperature in a solvent-free or low-solvent environment by using sulfuric acid as catalyst.

Magnetic CoFe2O4 nanoparticle immobilized N-propyl diethylenetriamine sulfamic acid as an efficient and recyclable catalyst for the synthesis of amides via the Ritter reaction

A magnetic CoFe2O4 nanoparticle immobilized diamine-N-sulfamic acid (CoFe2O4@SiO2-DASA) was synthesized and used as efficient heterogeneous catalyst for the synthesis of amides via the Ritter reaction under solvent-free conditions. The magnetic nanocatalyst could be readily recovered by applying an external magnet and recycled several times without considerable loss of its catalytic activity.

NH2 as a directing group: From the cyclopalladation of amino esters to the preparation of benzolactams by palladium(II)-catalyzed carbonylation of N-unprotected arylethylamines

An unusual NH2-directed Pd(II)-catalyzed carbonylation of quaternary aromatic α-amino esters to yield benzolactams has been developed. The steric hindrance around the amino group is pivotal for the success of the process. The stoichiometric cyclometalation of a variety amino esters has been studied in order to evaluate the influence of the different variables (size of the metallacycle, aromatic ring substituents, and steric bulk) in the process, and a complete kinetico-mechanistic study of the cyclopalladation process has been carried out. The experimental results indicate that the full substitution of the carbon in the α position of the amino esters plays an important role in their cyclopalladation reaction. The reaction shows a strong bias toward six-membered lactams over the five-membered analogues, which can be explained by a greater reactivity of the six-membered palladacycles.

(ALPHA-SUBSTITUTED ARALKYLAMINO AND HETEROARYLALKYLAMINO) PYRIMIDINYL AND 1,3,5-TRIAZINYL BENZIMIDAZOLES, PHARMACEUTICAL COMPOSITIONS THEREOF, AND THEIR USE IN TREATING PROLIFERATIVE DISEASES

Provided herein are (alpha-substituted aralkylamino or heteroarylalkylamino) pyrimidinyl and 1,3,5-triazinyl benzimidazoles, e.g., a compound of Formula 1, and their pharmaceutical compositions, preparation, and use as agents or drugs for treating proliferative diseases

Pd(ii)-catalyzed carbonylation of N-unprotected arylethylamines

An unprecedented NH2-directed Pd(ii)-catalytic carbonylation of quaternary aromatic α-amino esters to yield 6-membered benzolactams has been developed. The reaction shows a strong bias to 6-membered lactams over 5-membered ones. The steric hind

Use of 5-hydroxy-4H-benzo[1,4]oxazin-3-ones as β2-adrenoceptor agonists

Novel β2-agonists with a 5-hydroxy-4H-benzo[1,4]oxazin-3-one moiety as head group are described. Systematic chemical variations at the phenethylamine residue of these compounds lead to the discovery of compound 6m as potent, full agonist of the β2-adrenoceptor with a high β1/β2-selectivity. Molecular modeling revealed an interaction between the carboxylic acid group of 6m and a lysine residue (K305) of the β2-receptor as putative explanation for the high observed selectivity. Further, compound 6m displayed in a guinea pig in vivo model a complete reversal of acetylcholine induced bronchoconstriction which lasted over the complete study time of 5 h.

Thiadiaziridine 1,1-Dioxides: Synthesis and Chemistry

The synthesis and chemical reactions of a series of thiadiaziridine 1,1-dioxides (2) are described.The thermal stability is highly dependent on the R group and in one case (R = tert-octyl) is postulated that the thermolysis initially produces a diradical intermediate which can be trapped or further fragments to give a nitrene.A temperature-dependent NMR study on the coalescence of the diastereotopic α-methyl protons of 2b gives a ΔG = 20 kcal*mol-1.

RADICAL STABILIZING EFFECTS. A COMPARISON OF TRANSITION STATE EFFECTS (RATES OF AZOALKANE DECOMPOSITIONS) WITH CALCULATED (AB INITIO) PI SPIN DENSITIES

Rate studies on five azoalkanes (4a-e) have been studied to assess important radical stabilizing effects.MO calculations of spin densities for three radicals with pi systems are correlated with kinetic rates of radical formation.