2275-84-5

Upstream product

• 13663-06-4 1-chloro-4-(2-chloro-propyl)-benzene 
• 77287-34-4 formamide 
• 5586-88-9 1-(4-chlorophenyl)propan-2-one 
• 1454-65-5 1-(4-chlorophenyl)propan-2-one oxime 
• 104-88-1 4-chlorobenzaldehyde 
• 1351781-72-0 C₁₂H₁₆ClNO₂ 
• 107-87-9 2-Pentanone 
• 64-12-0 p-Chloroamphetamine 
• 710-20-3 1-chloro-4-(2-nitropropenyl)benzene 
• 3938-96-3 ethyl 2-methoxyacetate 
• 29125-75-5 p-chloro(methylstyrene) 
• 108-90-7 chlorobenzene 

Downstream Products

• 71271-86-8 N-Methansulfonyl-1-(4-chlorphenyl)-2-aminopropan 
• 71271-88-0 1-[2-(4-Chloro-phenyl)-1-methyl-ethyl]-3-methyl-thiourea 
• 13026-05-6 Bis-[2-(4-chloro-phenyl)-1-methyl-ethyl]-amine 
• 65115-00-6 (+/-)-N_.N-Dimethyl-p-chloramphetamin 
• 1199-85-5 p-Chlorometamphetamine 
• 84499-80-9 (S)-(+)-N_.N-Dimethyl-p-chloramphetamin 

Relevant academic research and scientific papers

Asymmetric Synthesis of Chiral Halogenated Amines using Amine Transaminases

Amine transaminases (ATAs) are versatile and industrially relevant biocatalysts that catalyze the transfer of an amine group from a donor to an acceptor molecule. Asymmetric synthesis from a prochiral ketone is the most preferred route to the desired amine product, as it is obtainable in a theoretical yield of 100 %. In addition to the requirement of active and enantioselective ATAs, the choice of a suitable amine donor is also important to save costs and to avoid additional enzymes to shift the equilibrium and/or to recycle the cofactors. In this work, we identified suitable (R)- and (S)-ATAs from Aspergillus fumigatus and Silicibacter pomeroyi, respectively, to afford a set of halogen-substituted derivatives of brominated or chlorinated 1-phenyl-2-propanamine, 4-phenylbutan-2-amine, and 1-(3-pyridinyl)ethanamine. Optimization of the donor–acceptor ratio enabled application of isopropylamine as an amine donor, which resulted in high conversions and amines with 73–99 % ee.

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.

Development of an engineered thermostable amine dehydrogenase for the synthesis of structurally diverse chiral amines

Amine dehydrogenases (AmDHs) are emerging as a class of attractive biocatalysts for synthesizing chiral amines via asymmetric reductive amination of ketones with inexpensive ammonia as an amino donor. However, the AmDHs developed to date exhibit limited substrate scope. Here, using directed evolution, we engineered a GkAmDH based on a thermostable phenylalanine dehydrogenase from Geobacillus kaustophilus. The newly developed AmDH is able to catalyze reductive amination of a diverse set of ketones and functionalized hydroxy ketones with ammonia or primary amines with up to >99% conversion, thus accessing structurally diverse chiral primary and secondary amines and chiral vicinal amino alcohols, with excellent enantioselectivity (up to >99% ee) and releasing water as the sole by-product.

An Ammonium-Formate-Driven Trienzymatic Cascade for ω-Transaminase-Catalyzed (R)-Selective Amination

(R)-Amination mediated by (R)-specific ω-transaminases generally requires costly d-alanine in excess to obtain the desired chiral amines in high yield. Herein, a one-pot, trienzymatic cascade comprising an (R)-specific ω-transaminase, an amine dehydrogenase, and a formate dehydrogenase was developed for the economical and eco-friendly synthesis of (R)-chiral amines. Using inexpensive ammonium formate as the sole sacrificial agent, the established cascade system enabled efficient ω-transaminase-mediated (R)-amination of various ketones, with high conversions and excellent ee (>99%); water and CO2 were the only waste products.

Enzymatic enantiomeric resolution of phenylethylamines structurally related to amphetamine

Both enantiomers of several phenylethylamines, structurally related to amphetamine, have been prepared in good yields and excellent enantiomeric purity by enzymatic kinetic resolution using CAL-B and ethyl methoxyacetate as the acyl donor. In the case of the 4-hydroxyderivative of amphetamine (compound 4i), the S enantiomer racemized possibly in a dynamic kinetic resolution (DKR) under the enzymatic conditions used. The Royal Society of Chemistry 2011.

Method of treating nausea and vomiting with certain substituted-phenylalkylamino (and aminoacid) derivatives and other serotonin depleting agents

A method for the treatment of emesis in a mammal, which method comprises administering to said mammal an emesis inhibiting amount of a compound which depletes serotonin in the brain of mammals; among which are compounds having the formula: STR1 wherein, R is selected from hydrogen, loweralkyl, trifluoromethyl, carboxyl, or loweralkoxycarbonyl; R1 and R2 are hydrogen or loweralkyl; Z is trifluoromethyl or halogen; the optical isomers and pharmaceutically acceptable salts thereof; two of the preferred compounds of the invention are fenfluramine and norfenfluramine.

Derivatives related to betaxolol with α- and β-adrenergic activities

The paper describes the synthesis and the pharmacological evaluation of some derivatives of betaxolol, all with an N-aralkylamine instead of the tertiobutylamine. These compounds have been tested for β1-adrenergic receptor antagonism on guinea pig atria, β2-adrenergic receptor antagonism on guinea pig trachea and α-adrenergic blocking activity on rat aorta. Compound U12 with a marked α-blocking activity and compound R8 with a β1/α ratio = 1 were selected for a haemodynamic study in the dog. The decrease in cardiac work and the diminution of total peripheral resistance exhibited by U12 are consistent with a dual α/β-blocking agent. Finally, structure-activity relationships are discussed.

Heterocyclic analogs of amphetamine: Thioureas, dithiocarbamates, and negatively substituted amides

A series of heterocyclic analogs of amphetamine was synthesized. The heterocycles employed included the 2-furyl, 2-thienyl, 3-methyl-2 thienyl, 3-pyridyl, and 6-methyl-2-pyridyl rings. The aliphatic amine group was converted to the N-methylthiourea, dithiocarbamate, methanesulfonyl, trifluoromethanesulfonyl, and trifluoroacetyl functions since similar conversions of the β-phenethylamine structure had shown blood pressure-lowering effects and some loss of behavioral effects. P-Chlorophenyl and 1-naphthyl analogs were also converted to these derivatives. Behavioral and other biological effects, including antiarthritic, passive cutaneous anaphylactic, and antimicrobial, were observed. The 3-methyl-2-thienyl analog of amphetamine significantly increased papillary muscle contractile force without producing arrhythmias.