931115-08-1

Basic information

• Product Name: (3S)-1-methyl-3-phenylpiperazine
• Synonyms: (3S)-1-methyl-3-phenylpiperazine
• CAS NO: 931115-08-1
• Molecular Weight: 176.261
• Mol File: 931115-08-1.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: (3S)-1-methyl-3-phenylpiperazine(CAS DataBase Reference)
• NIST Chemistry Reference: (3S)-1-methyl-3-phenylpiperazine(931115-08-1)
• EPA Substance Registry System: (3S)-1-methyl-3-phenylpiperazine(931115-08-1)

Safety Data

• Hazardous Substances Data: 931115-08-1(Hazardous Substances Data)

Usage

General Description

(3S)-1-methyl-3-phenylpiperazine is a chemical compound with a molecular formula of C11H16N2. It is a piperazine derivative, which is a class of organic compounds commonly used as pharmaceuticals and in the synthesis of other chemicals. The compound has a chiral center, making it exist as a pair of enantiomers. Its structure consists of a piperazine ring with a methyl group and a phenyl group attached to it. (3S)-1-methyl-3-phenylpiperazine is used in the pharmaceutical industry for its potential application in the treatment of central nervous system disorders. It may also have potential use as an intermediate in the synthesis of other organic compounds. Due to its biological activity and potential therapeutic applications, this compound is of interest to researchers and pharmaceutical companies.

Upstream product

• 623-03-0 4-Cyanochlorobenzene 
• 5271-27-2 1-methyl-3-phenylpiperazine 
• 2900-27-8 (2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethanoic acid 
• 6956-56-5 2,2-dimethoxy-1-phenylethanone 
• 15206-55-0 methyl 2-oxo-2-phenylacetate 
• 90915-03-0 3-phenyl-5,6-dihydropyrazin-2(1H)-one 
• 1346681-71-7 (1E)-4-hydroxy-1-mesityl-4-methylpent-1-en-3-one 
• 1048380-66-0 (S)-1-methyl-3-phenylpiperazine (+)-anicyphos salt 
• 931115-07-0 (S)-1-methyl-3-phenylpiperazine-2,5-dione 
• 960403-77-4 1-methyl-3-phenylpiperazine ethyloxamate 
• 131543-46-9 Glyoxal 
• 79513-96-5 (S)-N¹-methyl-2-phenylethane-1,2-diamine 
• 1074-12-0 phenylglyoxal hydrate 
• 109-81-9 N-methyl-ethane-1,2-diamine 

Downstream Products

• 931115-11-6 2-[(2S)-4-methyl-2-phenyl-1-piperazinyl]-3-pyridinecarbonitrile 
• 931115-10-5 (S)-1-methyl-3-phenylpiperazine oxalate 

Relevant articles and documents

Low-Temperature Nickel-Catalyzed C?N Cross-Coupling via Kinetic Resolution Enabled by a Bulky and Flexible Chiral N-Heterocyclic Carbene Ligand

The transition-metal-catalyzed C?N cross-coupling has revolutionized the construction of amines. Despite the innovations of multiple generations of ligands to modulate the reactivity of the metal center, ligands for the low-temperature enantioselective amination of aryl halides remain a coveted target of catalyst engineering. Designs that promote one elementary reaction often create bottlenecks at other steps. We here report an unprecedented low-temperature (as low as ?50 °C), enantioselective Ni-catalyzed C?N cross-coupling of aryl chlorides with sterically hindered secondary amines via a kinetic resolution process (s factor up to >300). A bulky yet flexible chiral N-heterocyclic carbene (NHC) ligand is leveraged to drive both oxidative addition and reductive elimination with low barriers and control the enantioselectivity. Computational studies indicate that the rotations of multiple σ-bonds on the C2-symmetric chiral ligand adapt to the changing needs of catalytic processes. We expect this design would be widely applicable to diverse transition states to achieve other challenging metal-catalyzed asymmetric cross-coupling reactions.

Biocatalytic Access to Piperazines from Diamines and Dicarbonyls

Given the widespread importance of piperazines as building blocks for the production of pharmaceuticals, an efficient and selective synthesis is highly desirable. Here we show the direct synthesis of piperazines from 1,2-dicarbonyl and 1,2-diamine substrates using the R-selective imine reductase from Myxococcus stipitatus as biocatalyst. Various N- and C-substituted piperazines with high activity and excellent enantioselectivity were obtained under mild reaction conditions reaching up to 8.1 g per liter.

Synthesis of Chiral Piperazines via Hydrogenation of Pyrazines Activated by Alkyl Halides

A facile method has been developed for the synthesis of chiral piperazines through Ir-catalyzed hydrogenation of pyrazines activated by alkyl halides, giving a wide range of chiral piperazines including 3-substituted as well as 2,3- and 3,5-disubstituted