68164-04-5

Usage

Uses

Used in Pharmaceutical Industry:
Benzenepropanamine, a-methyl-N-(phenylmethyl)is used as a therapeutic agent for treating attention deficit hyperactivity disorder (ADHD) and narcolepsy due to its ability to increase the release of neurotransmitters, which improves cognitive function and reduces symptoms of these conditions.
Used in Off-Label Applications:
Although not its primary intended use, Benzenepropanamine, a-methyl-N-(phenylmethyl)is sometimes used off-label as a performance-enhancing drug or for recreational purposes. Its stimulating and euphoric effects can temporarily increase alertness and energy levels, although this misuse can lead to serious health risks, including addiction, tolerance, and potentially severe side effects such as increased heart rate, high blood pressure, and psychosis.
Controlled Substance Classification:
Due to its high potential for abuse and addiction, Benzenepropanamine, a-methyl-N-(phenylmethyl)is classified as a Schedule II controlled substance in the United States, indicating the need for strict regulation and control over its distribution and use.

Upstream product

• 2550-26-7 4-Phenyl-2-butanone 
• 100-46-9 benzylamine 
• 18720-46-2 benzylamine hydrogenperchlorate 
• 109-73-9 N-butylamine 
• 74-89-5 methylamine 
• 1353675-02-1 (3-hydroperoxy-3-methoxybutyl)benzene 
• 22374-89-6 (RS)-1-methyl-3-phenylpropylamine 
• 100-52-7 benzaldehyde 
• 83167-23-1 Benzyl-[1-methyl-3-phenyl-prop-(E)-ylidene]-amine 

Downstream Products

• 81760-40-9 5-[1-Hydroxy-2-(1-methyl-3-phenyl-propylamino)-ethyl]-2-methyl-benzenesulfonamide 
• 344754-64-9 5-{2-[Benzyl-(1-methyl-3-phenyl-propyl)-amino]-acetyl}-2-propyl-benzenesulfonamide 
• 345947-69-5 3-{2-[Benzyl-(1-methyl-3-phenyl-propyl)-amino]-acetyl}-benzenesulfonamide 
• 22374-89-6 (RS)-1-methyl-3-phenylpropylamine 
• 76805-38-4 1-(4-ethoxycarbonylmethylphenoxy)-3-(1-methyl-3-phenylpropylamino)-2-propanol 
• 68504-99-4 2-amino-5-[1-hydroxy-2-[N-(1-methyl-3-phenylpropyl)-N-(phenylmethyl)amino]ethyl]benzenesulphonamide 
• 1260510-57-3 C₁₀H₁₀O₄*C₁₇H₂₁N 
• 4187-57-9 (S)-1-methyl-3-phenylpropylamine 
• 937-52-0 (R)-1-methyl-3-phenylpropylamine 
• 1380487-91-1 N-benzyl-N-methyl-4-phenylbutan-2-amine 
• 344752-02-9 5-{2-[Benzyl-(1-methyl-3-phenyl-propyl)-amino]-acetyl}-2-methoxy-benzenesulfonamide 
• 81580-34-9 (S)-α-methylbenzenepropanamine hydrochloride 
• 826-16-4 (+)-(R)-α-methylbenzenepropanamine hydrochloride 
• 1332828-01-9 (S)-2,2,2-trifluoro-N-(4-phenylbutan-2-yl)acetamide 

Relevant academic research and scientific papers

Carbon monoxide-driven osmium catalyzed reductive amination harvesting WGSR power

Herein, we present the first example of Os-catalyzed efficient reductive amination under water-gas shift reaction conditions. The developed catalytic systems are formedin situin aqueous solutions, employ as small as 0.0625 mol% osmium and are capable of delivering reductive amination products for a broad range of aliphatic and aromatic carbonyl compounds and amines. The scope of the reaction, active catalytic systems, possible limitations of the method and DFT-supported mechanistic considerations are discussed in detail in the manuscript.

Intramolecular C?H Amination of N-Alkylsulfamides by tert-Butyl Hypoiodite or N-Iodosuccinimide

1,3-Diamines are an important class of compounds that are broadly found in natural products and are also widely used as building blocks in organic synthesis. Although the intramolecular C?H amination of N-alkylsulfamide derivatives is a reliable method for the construction of 1,3-diamine structures, the majority of these methods involve the use of a transition-metal catalyst. We herein report on a new transition-metal-free method using tert-butyl hypoiodite (t-BuOI) or N-iodosuccinimide (NIS), enabling secondary non-benzylic and tertiary C?H amination reactions to proceed. The cyclic sulfamide products can be easily transformed into 1,3-diamines. Mechanistic investigations revealed that amination reactions using t-BuOI or NIS each proceed via different pathways.

CATALYST COMPOUNDS

The present invention relates to an iridium-based catalyst compound for hydrogenating reducible moieties, especially imines and iminiums, the catalyst compounds being defined by the formulas: where ring B is either itself polycyclic, or ring B together with R is polycyclic. The catalysts of the invention are particularly effective in reductive amination procedures 10 which involve the in situ generation of the imine or iminium under reductive hydrogenative conditions.

Fast reductive amination by transfer hydrogenation "on water"

Reductive amination of various ketones and aldehydes by transfer hydrogenation under aqueous conditions has been developed, by using cyclometallated iridium complexes as catalysts and formate as hydrogen source. The pH value of the solution is shown to be critical for a high catalytic chemoselectivity and activity, with the best pH value being 4.8. In comparison with that in organic solvents, the reductive amination in an aqueous phase is faster, and the molar ratio of the substrate to the catalyst (S/C) can be set as high as 1×105, the highest S/C value ever reported in reductive amination reactions. The catalyst is easy to access and the reaction is operationally simple, allowing a wide range of ketones and aldehydes to react with various amines in high yields. The protocol provides a practical and environmental friendly new method for the synthesis of amine compounds. Greener amine synthesis: A versatile reductive amination protocol has been developed. By using an iridium catalyst in water, a broad range of ketones and aldehydes react with amines to afford various new amines in good yields (see scheme), with molar ratios of the substrate to the catalyst (S/C) as high as 1×10 5. The pH of the reaction solution plays a key role, regulating both the catalytic activity and the selectivity. Copyright

CATALYST COMPOUNDS

The present invention relates to an iridium-based catalyst compound for hydrogenating reducible moieties, especially imines and iminiums, the catalyst compounds being defined by the formulas: where ring B is either itself polycyclic, or ring B together with R is polycyclic. The catalysts of the invention are particularly effective in reductive amination procedures 10 which involve the in situ generation of the imine or iminium under reductive hydrogenative conditions.

Sequential reductive amination-hydrogenolysis: A one-pot synthesis of challenging chiral primary amines

Difficult-to-access chiral primary amines were formed in good to high yield and ee using a rare example of a one-pot synthesis from prochiral ketones (sequential reductive amination-hydrogenloysis). As a highlight we also demonstrate a one-pot reductive amination-hydrogenolysis-reductive amination (five reactions) of ortho-methoxyacetophenone resulting in the chiral diamine 1-(2-methoxyphenyl)ethyl-(2-pyridylmethyl)-amine (4) (58% overall yield, >99% ee), a new organocatalyst for aqueous enantioselective aldol reactions. Copyright

A mild one-pot conversion of alkenes into amines through tandem ozonolysis and reductive amination

The selective reduction of hydroperoxyacetals to aldehydes by sodium triacetoxyborohydride provides the basis for a mild one-pot synthesis of amines from alkenes. Georg Thieme Verlag Stuttgart.

The reductive amination of aldehydes and ketones by catalytic use of dibutylchlorotin hydride complex

The reductive amination of aldehydes or ketones using Ph 2SiH2 or PhSiH3 has been effectively promoted by the direct use of Bu2SnClH-pyridine N-oxide as a catalyst; this method has advantages in terms of its mild conditions and wide application to various carbonyls and amines, including aliphatic examples. The Royal Society of Chemistry 2006.

Efficient preparation of N-benzyl secondary amines via benzylamine-borane mediated reductive amination

An efficient one-pot reductive amination protocol for preparing N-benzyl secondary amines is described.

Reductive amination promoted by tributyltin hydride

Reductive amination of carbonyl compounds with primary and secondary ammonium salts was performed by tributyltin hydride in DMF solvent at room temperature. A variety of secondary and tertiary amines including sterically hindered ones could be synthesized in one-pot procedure. No side reaction such as the reduction of starting carbonyl or overalkylation was detected.