5271-27-2

Basic information

• Product Name: 1-Methyl-3-phenylpiperazine
• Synonyms: 1-N-METHYL-3-PHENYL-PIPERAZINE;1-METHYL-3-PHENYLPIPERAZINE;Piperazine, 1-methyl-3-phenyl- (7CI,8CI,9CI);(3S)-1-methyl-3-phenyl-2,3,5,6-tetrahydropyrazine;1-Methyl-3-phenyl;1-Methyl-3-phenylpiperazine 97%;(+/-)-3-Phenyl-1-methylpiperazine;1-Methyl-3-phenylpiperazine ,98%
• CAS NO: 5271-27-2
• Molecular Formula: C₁₁H₁₆N₂
• Molecular Weight: 176.26
• EINECS: 432-360-3
• Product Categories: PIPERIDINE;Piperidines, Piperidones, Piperazines;Piperaizine;Piperazine derivates;Aromatics;Heterocycles;Building Blocks;Heterocyclic Building Blocks;Piperazines
• Mol File: 5271-27-2.mol
• Article Data: 6

Chemical Properties

• Melting Point: 56-60 °C(lit.)
• Boiling Point: 85 °C
• Flash Point: 85°C/0.5mm
• Appearance: Pale yellow/Needles or Crystals
• Density: 0.991 g/cm³
• Vapor Pressure: 0.00382mmHg at 25°C
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 8.52±0.40(Predicted)
• Water Solubility: soluble
• Sensitive: Air Sensitive
• CAS DataBase Reference: 1-Methyl-3-phenylpiperazine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Methyl-3-phenylpiperazine(5271-27-2)
• EPA Substance Registry System: 1-Methyl-3-phenylpiperazine(5271-27-2)

Safety Data

• Hazard Codes: T,Xi
• Statements: 25-34-36/37/38
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2923 8/PG 3
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 5271-27-2(Hazardous Substances Data)

Usage

Uses

Used in Forensic Laboratories:
1-Methyl-3-phenylpiperazine is used as reference materials for forensic laboratories. It is utilized in the analysis and identification of substances related to criminal investigations, particularly due to its effects on the central and autonomic nervous systems, blood pressure, and smooth muscle.
Used in Pharmaceutical Research:
Although not explicitly mentioned in the provided materials, 1-Methyl-3-phenylpiperazine, being a piperazine derivative, may also have potential applications in the development of pharmaceuticals targeting the central nervous system, given its effects on these systems. Further research and development would be required to explore and validate these potential uses.

InChI:InChI=1/C11H16N2/c1-13-8-7-12-11(9-13)10-5-3-2-4-6-10/h2-6,11-12H,7-9H2,1H3/p+2/t11-/m1/s1

Upstream product

• 100-58-3 phenylmagnesium bromide 
• 109-01-3 1-methyl-piperazine 
• 799796-66-0 1-methyl-2-oxo-3-phenylpiperazine 
• 23174-98-3 1-benzyl-4-methyl-2-phenyl-piperazine 

Downstream Products

• 61337-88-0 3-cyano-2-(4-methyl-2-phenyl-1-piperazynyl)pyridine 
• 333738-24-2 2-(4-methyl-3-phenylpiperazinyl)pyridine-3-carbonitrile 
• 1174064-76-6 C₂₂H₁₈N₆ 
• 5271-29-4 1,4-dimethyl-2-phenylpiperazine 
• 1174064-73-3 1-(2-cyanophenyl)-2-oxohydropyridine-3-carbonitrile 
• 1072159-75-1 1-methyl-3-phenylpiperazine hydrochloride 
• 931115-08-1 (3S)-1-methyl-3-phenylpiperazine 
• 960403-87-6 (3R)-1-methyl-3-phenylpiperazine 
• 1346681-93-3 (2S)-1-(3-mesitylpropanoyl)-4-methyl-2-phenylpiperazine 
• 1312573-30-0 2-(4-chlorophenyl)-1-(4-methyl-2-phenylpiperazin-1-yl)ethan-one 
• 1094259-06-9 3-chloro-6-(4-methyl-2-phenyl-1-piperazinyl)pyridazine 
• 1048380-66-0 (S)-1-methyl-3-phenylpiperazine (+)-anicyphos salt 
• 61338-13-4 2-(4-methyl-2-phenyl-1-piperazinyl)-3-pyridinecarboxylic acid 
• 61337-89-1 2-(4-methyl-2-phenylpiperazin-1-yl)-pyridine-3-methanol 

Relevant articles and documents

α-Functionalization of Cyclic Secondary Amines: Lewis Acid Promoted Addition of Organometallics to Transient Imines

Cyclic imines, generated in situ from their corresponding N-lithiated amines and a ketone hydride acceptor, undergo reactions with a range of organometallic nucleophiles to generate α-functionalized amines in a single operation. Activation of the transient imines by Lewis acids that are compatible with the presence of lithium alkoxides was found to be crucial to accommodate a broad range of nucleophiles including lithium acetylides, Grignard reagents, and aryllithiums with attenuated reactivities.

Process for preparing 1-methyl-3-phenylpiperazine using a novel intermediate

The present invention describes an industrially advantageous process to prepare highly pure 1-Methyl-3-phenylpiperazine of Formula I that makes use of a novel piperazine derivative, 4-Benzyl-1-methyl-2-oxo-3-phenylpiperazine, represented by Formula II 1-Methyl-3-phenylpiperazine is a useful intermediate in the preparation of antidepressant Mirtazapine.

INTERMEDIATE COMPOUNDS FOR THE PREPARATION OF MIRTAZAPINE AND THE PRODUCTION METHODS THEREOF

Intermediate compounds for the preparation of mirtazapine and obtention methods thereof. A method is described for obtaining (±)-3-phenyl-1-methylpiperazine, an important intermediate for obtaining mirtazapine, which is based on imposing a cyclation reaction, in the presence of a reducing agent, on new compounds of general formula (I) in which Z is a leaving group capable of undergoing a nucleophylic displacement. A method is also described for obtaining the new compounds of formula (I).

Novel method for the preparation of piperazine and its derivatives

A novel method for the synthesis of piperazine and its derivatives of formula 1, 1wherein R is selected from hydrogen, or a lower alkyl group having 1 to 6 carbon atoms or a phenylalkyl group the alkyl of which has 1 to 4 carbon atoms; R1 is selected from hydrogen, a methyl group, a phenyl group optionally substituted with an alkyl group having 1 to 6 carbon atoms, or a phenylalkyl group the alkyl of which has 1 to 4 carbon atoms; and R2 is selected from hydrogen, or a methyl group, or a fluoromethyl group; 2comprising the steps: a. reacting an ester of formula 11 with substituted or unsubstituted ethylenediamine of formula 7 to give 3,4-dehydropiperazine-2-one and its derivatives of formula 12, wherein R, R1, R2 are as defined above and R6 is a C1 to C4 linear or branched alkyl group; and b. reacting the 3,4-dehydro-piperazine-2-one and its derivatives of formula 12 with a reducing agent to yield the piperazine and its derivatives of formula 1.

Process for preparing piperazine derivatives

A process for preparing a piperazine derivative represented by the formula (V): comprising reacting 1-methyl-3-phenylpiperazine with 2-chloro-3-cyanopyridine in an aprotic polar organic solvent in the presence of a base and an alkali metal halide. The piperazine derivative and its oxalate are compounds useful as preparation intermediates of mirtazapine.

Synthesis of piperazine ring

A novel process for preparing a compound of the formula I: whereinR1 denotes substituted or unsubstituted alkyl, alkoxy, aryl, aryloxy or arylalkoxy; R2 denotes substituted or unsubstituted alkyl, alkoxy, aryl, aryloxy, arylalkoxy, tosyl, formyl, acetyl or amine; and R3 denotes substituted or unsubstituted alkyl, alkoxy, aryl, aryloxy or arylalkoxy is disclosed. These compounds are useful in the synthesis of the antidepressant mirtazapine and other tetracyclic compounds.