60-15-1

Usage

Safety Profile

Poison by ingestion,subcutaneous, intravenous, and intraperitoneal routes.Human systemic effects by ingestion: excitement, changesin heart rate and sweating. When heated to decompositionit emits very toxic fumes of NOx. See other amphetamineentries.

InChI:InChI=1/C9H13N/c1-2-4-8-5-3-6-9(10)7-8/h3,5-7H,2,4,10H2,1H3

Upstream product

• 17019-26-0 (E)-2-(hydroxyimino)-1-phenylpropan-1-one 
• 156-34-3 l-amphetamine 
• 5171-99-3 (1-phenylpropan-2-ylidene)hydrazine 
• 7499-19-6 2-methyl-2-phenylpropionamide 
• 10304-81-1 1-phenyl-2-chloropropane 
• 55-52-7 pheniprazine 
• 81136-08-5 2-methyl-3-phenylpropanoyl chloride 
• 14593-16-9 N-acetylamphetamine 
• 77287-34-4 formamide 
• 103-79-7 1-phenyl-acetone 
• 13213-36-0 1-phenylpropan-2-one oxime 
• 98-71-5 4-hydrazino-benzenesulfonic acid 
• 540-69-2 ammonium formate 
• 705-60-2 (2-nitroprop-1-enyl)benzene 

Downstream Products

• 26393-84-0 bis-(2-hydroxy-ethyl)-(1-methyl-2-phenyl-ethyl)-amine 
• 63918-85-4 2-(1-methyl-2-phenyl-ethylamino)-ethanol 
• 20640-10-2 N-(1-Methyl-2-phenyl-ethyl)-β-mercapto-ethylamin 
• 108303-14-6 N-(1-methyl-2-phenyl-ethyl)-ethylenediamine 
• 105340-05-4 1-(1-methyl-2-phenyl-ethyl)-imidazolidin-2-one 
• 139-68-4 (+/-)-nicotinic acid-(1-methyl-2-phenyl-ethylamide) 
• 15855-02-4 N-α-Methylphenethyl-n-pyridincarboxamid 
• 40302-91-8 (+/-)-N-(1-methyl-2-phenyl-ethyl)-furan-2-carboxamide 
• 100710-59-6 (+/-)-N-(1-methyl-2-phenyl-ethyl)-thiophene-2-carboxamide 
• 93315-98-1 2-(1-methyl-2-phenylethyl)-1H-isoindole-1,3(2H)-dione 
• 7632-10-2 methamphetamin 
• 4075-96-1 1-phenyl-2-dimethylaminopropane 
• 3319-00-4 (+/-)-1-(1-methyl-2-phenylethyl)piperidine 
• 100369-88-8 optically inactive N-(1-methyl-2-phenyl-ethyl)-lactamide 

Relevant academic research and scientific papers

Markovnikov Wacker-Tsuji Oxidation of Allyl(hetero)arenes and Application in a One-Pot Photo-Metal-Biocatalytic Approach to Enantioenriched Amines and Alcohols

The Wacker-Tsuji aerobic oxidation of various allyl(hetero)arenes under photocatalytic conditions to form the corresponding methyl ketones is presented. By using a palladium complex [PdCl2(MeCN)2] and the photosensitizer [Acr-Mes]ClO4 in aqueous medium and at room temperature, and by simple irradiation with blue led light, the desired carbonyl compounds were synthesized with high conversions (>80%) and excellent selectivities (>90%). The key process was the transient formation of Pd nanoparticles that can activate oxygen, thus recycling the Pd(II) species necessary in the Wacker oxidative reaction. While light irradiation was strictly mandatory, the addition of the photocatalyst improved the reaction selectivity, due to the formation of the starting allyl(hetero)arene from some of the obtained by-products, thus entering back in the Wacker-Tsuji catalytic cycle. Once optimized, the oxidation reaction was combined in a one-pot two-step sequential protocol with an enzymatic transformation. Depending on the biocatalyst employed, i. e. an amine transaminase or an alcohol dehydrogenase, the corresponding (R)- and (S)-1-arylpropan-2-amines or 1-arylpropan-2-ols, respectively, could be synthesized in most cases with high yields (>70%) and in enantiopure form. Finally, an application of this photo-metal-biocatalytic strategy has been demonstrated in order to get access in a straightforward manner to selegiline, an anti-Parkinson drug. (Figure presented.).

ASPARAGINE DERIVATIVES AND METHODS OF USE THEREOF

The present invention relates to compounds of formulas (A) and (I), pharmaceutically acceptable salts thereof, and solvates of any of them, pharmaceutical compositions comprising them, methods of preparation thereof, intermediate compounds useful for the preparation thereof, and methods of treatment or prophylaxis of diseases, in particular cancer, such as colorectal cancer, using these. (A) (I)

Direct Access to Primary Amines from Alkenes by Selective Metal-Free Hydroamination

Direct and selective synthesis of primary amines from easily available precursors is attractive yet challenging. Herein, we report the rapid synthesis of primary amines from alkenes via metal-free regioselective hydroamination at room temperature. Ammonium carbonate was used as ammonia surrogate for the first time, allowing for efficient conversion of terminal and internal alkenes into linear, α-branched, and α-tertiary primary amines under mild conditions. This method provides a straightforward and powerful approach to a wide spectrum of advanced, highly functionalized primary amines which are of particular interest in pharmaceutical chemistry and other areas.

Transaminase-mediated synthesis of enantiopure drug-like 1-(3′,4′-disubstituted phenyl)propan-2-amines

Transaminases (TAs) offer an environmentally and economically attractive method for the direct synthesis of pharmaceutically relevant disubstituted 1-phenylpropan-2-amine derivatives starting from prochiral ketones. In this work, we report the application of immobilised whole-cell biocatalysts with (R)-transaminase activity for the synthesis of novel disubstituted 1-phenylpropan-2-amines. After optimisation of the asymmetric synthesis, the (R)-enantiomers could be produced with 88-89% conversion and >99% ee, while the (S)-enantiomers could be selectively obtained as the unreacted fraction of the corresponding racemic amines in kinetic resolution with >48% conversion and >95% ee. This journal is

ENVIRONMENTALLY-FRIENDLY HYDROAZIDATION OF OLEFINS

The present invention provides processes for the synthesis of organic azides, intermediates for the production thereof, and compositions related thereto.

Stereoselective Synthesis of 1-Arylpropan-2-amines from Allylbenzenes through a Wacker-Tsuji Oxidation-Biotransamination Sequential Process

Herein, a sequential and selective chemoenzymatic approach is described involving the metal-catalysed Wacker-Tsuji oxidation of allylbenzenes followed by the amine transaminase-catalysed biotransamination of the resulting 1-arylpropan-2-ones. Thus, a series of nine optically active 1-arylpropan-2-amines were obtained with good to very high conversions (74–92%) and excellent selectivities (>99% enantiomeric excess) in aqueous medium. The Wacker-Tsuji reaction has been exhaustively optimised searching for compatible conditions with the biotransamination experiments, using palladium(II) complexes as catalysts and iron(III) salts as terminal oxidants in aqueous media. The compatibility of palladium/iron systems for the chemical oxidation with commercially available and made in house amine transaminases was analysed, finding ideal conditions for the development of a general and stereoselective cascade sequence. Depending on the selectivity displayed by selected amine transaminase, it was possible to produce both 1-arylpropan-2-amines enantiomers under mild reaction conditions, compounds that present therapeutic properties or can be employed as synthetic intermediates of chiral drugs from the amphetamine family. (Figure presented.).

AMPHETAMINE CONTROLLED RELEASE, PRODRUG, AND ABUSE-DETERRENT DOSAGE FORMS

The invention also relates to pharmaceutical compositions comprising highly pure amphetamine and amphetamine-class compounds resulting from the synthesis of chiral and racemic amphetamine derivatives by stereospecific, regioselective cuprate addition reaction with aziridine phosphoramidate compounds, and to methods of manufacturing, delivering, and using the amphetamine compounds resulting from the synthesis of chiral and racemic amphetamine derivatives by stereospecific, regioselective cuprate addition reaction with aziridine phosphoramidate compounds.

Ligand-Enabled meta-Selective C-H Arylation of Nosyl-Protected Phenethylamines, Benzylamines, and 2-Aryl Anilines

A Pd-catalyzed, meta-selective C-H arylation of nosyl-protected phenethylamines and benzylamines is disclosed using a combination of norbornene and pyridine-based ligands. Subjecting nosyl protected 2-aryl anilines to this protocol led to meta-C - H arylation at the remote aryl ring. A diverse range of aryl iodides are tolerated in this reaction, along with select heteroaryl iodides. Select aryl bromides bearing ortho-coordinating groups can also be utilized as effective coupling partners in this reaction. The use of pyridine ligands has allowed the palladium loading to be reduced to 2.5 mol %. Furthermore, a catalytic amount of 2-norbomene (20 mol %) to mediate this meta-C - H activation process is demonstrated for the first time. Utilization of a common protecting group as the directing group for meta-C-H activation of amines is an important feature of this reaction in terms of practical applications.

Hybrid Organo- and Biocatalytic Process for the Asymmetric Transformation of Alcohols into Amines in Aqueous Medium

A hybrid organo- and biocatalytic system for the asymmetric conversion of racemic alcohols into amines was developed. Combining an organocatalyst, AZADO, an oxidant, NaOCl, and an enzyme, ω-transaminase, we implemented a one-pot oxidation-transamination sequential process in aqueous medium. The method showed broad substrate scope and was successfully applied to conventional secondary alcohols and sterically hindered β-substituted cycloalkanols, where a highly stereoselective dynamic asymmetric bioamination enabled us to set up both contiguous stereocenters with very high enantio- and diastereomeric ratio (>90% yield, >99% ee, and up to 49:1 dr).