86073-42-9

Basic information

• Product Name: AcetaMide, N-[(1R)-2-(4-Methoxyphenyl)-1-Methylethyl]-
• Synonyms: AcetaMide, N-[(1R)-2-(4-Methoxyphenyl)-1-Methylethyl]-;N-[(2R)-1-(4-methoxyphenyl)propan-2-yl]acetamide
• CAS NO: 86073-42-9
• Molecular Formula: C₁₂H₁₇NO₂
• Molecular Weight: 207.26888
• Mol File: 86073-42-9.mol
• Article Data: 10

Chemical Properties

• Melting Point: 92-93 °C
• Boiling Point: 389.7±25.0 °C(Predicted)
• Appearance: /
• Density: 1.025±0.06 g/cm3(Predicted)
• PKA: 15.97±0.46(Predicted)
• CAS DataBase Reference: AcetaMide, N-[(1R)-2-(4-Methoxyphenyl)-1-Methylethyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: AcetaMide, N-[(1R)-2-(4-Methoxyphenyl)-1-Methylethyl]-(86073-42-9)
• EPA Substance Registry System: AcetaMide, N-[(1R)-2-(4-Methoxyphenyl)-1-Methylethyl]-(86073-42-9)

Safety Data

• Hazardous Substances Data: 86073-42-9(Hazardous Substances Data)

Usage

General Description

Acetamide, N-[(1R)-2-(4-methoxyphenyl)-1-methylethyl]-, also known as tapentadol, is a synthetic opioid analgesic used for the treatment of moderate to severe acute and chronic pain. It works by binding to the mu-opioid receptor in the central nervous system, resulting in pain relief. Tapentadol's unique dual mechanism of action combines mu-opioid receptor agonism with noradrenaline reuptake inhibition, providing effective pain relief with a lower risk of gastrointestinal side effects compared to traditional opioids. This medication is available in various formulations, including immediate-release and extended-release tablets, and is prescribed under close medical supervision due to its potential for dependence and abuse. Common side effects may include dizziness, nausea, constipation, and drowsiness.

Upstream product

• 64-13-1 2-amino-1-(4-methyoxyphenyl)propane 
• 141-78-6 ethyl acetate 
• 122-84-9 4-methoxybenzyl methyl ketone 
• 37629-51-9 1-methoxy-4-((E)-2-nitroprop-1-enyl)benzene 
• 123-11-5 4-methoxy-benzaldehyde 
• 108-24-7 acetic anhydride 
• 69390-41-6 (E)-N-(1-(4-methoxyphenyl)prop-1-en-2-yl)acetamide 
• 140-67-0 Estragole 

Downstream Products

• 58993-79-6 (R)-(-)-p-methoxyamphetamine 
• 73573-87-2 (R,R)-formoterol 
• 299964-43-5 (R)-1-(3-Amino-4-benzyloxy-phenyl)-2-[(R)-2-(4-methoxy-phenyl)-1-methyl-ethylamino]-ethanol 
• 245759-61-9 (R)-1-(4-Benzyloxy-3-nitro-phenyl)-2-[(R)-2-(4-methoxy-phenyl)-1-methyl-ethylamino]-ethanol 
• 408497-91-6 N-(2-Benzyloxy-5-{(R)-1-hydroxy-2-[(R)-2-(4-methoxy-phenyl)-1-methyl-ethylamino]-ethyl}-phenyl)-formamide 
• 112101-74-3 (R)-N-[1-(4-methoxy-3-sulfamoylphenylpropan-2-yl)]acetamide 

Relevant articles and documents

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.).

Design of phosphorus ligands with deep chiral pockets: Practical Synthesis of chiral β-arylamines by asymmetric hydrogenation

WingPhos, a C2-symmetric bisphosphorus ligand with a deep and well-defined chiral pocket was developed. It has shown high efficiency in the rhodium-catalyzed asymmetric hydrogenation of (E)-β-aryl-N-acetyl enamides, cyclic β-aryl enamides, and heterocyclic β-aryl enamides. A series of chiral β-arylisopropylamines, 2-aminotetralines, and 3-aminochromans can be synthesized with excellent ee values (nbd=3,5-norbornadiene; TON=turnover number). Copyright

Stereoselectivity of four (R)-selective transaminases for the asymmetric amination of ketones

Four (R)-ω-transaminases originating from Hyphomonas neptunium (HN-ωTA), Aspergillus terreus (AT-ωTA) and Arthrobacter sp. (ArR-ωTA), as well as an evolved transaminase (ArRmut11-ωTA) were successfully employed for the amination of prochiral ketones leading to optically pure (R)-amines. The first three transaminases displayed perfect stereoselectivity for the amination of all substrates tested (ee >99%). Furthermore, the transaminase AT-ωTA led in most cases to better conversion than ArR-ωTA and HN-ωTA using D-alanine as amine donor. α-Tetralone, which was the only substrate not accepted by HN-ωTA, ArR-ωTA, and AT-ωTA, was successfully transformed with perfect enantioselectivity (ee >99%) into the corresponding optically pure amine employing the variant ArRmut11-ωTA. Copyright