36939-28-3

Basic information

• Product Name: 1-methyl-2-phenylpiperidine
• Synonyms: 1-methyl-2-phenylpiperidine;(2R)-1-Methyl-2β-phenylpiperidine;N-Methyl-2-phenyl-D2-tetrahydropyridine
• CAS NO: 36939-28-3
• Molecular Formula: C₁₂H₁₇N
• Molecular Weight: 175.27008
• EINECS: 253-282-4
• Mol File: 36939-28-3.mol

Chemical Properties

• Boiling Point: 247°Cat760mmHg
• Flash Point: 94.2°C
• Appearance: /
• Density: 0.964g/cm³
• Vapor Pressure: 0.0263mmHg at 25°C
• Refractive Index: 1.526
• CAS DataBase Reference: 1-methyl-2-phenylpiperidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-methyl-2-phenylpiperidine(36939-28-3)
• EPA Substance Registry System: 1-methyl-2-phenylpiperidine(36939-28-3)

Safety Data

• Hazardous Substances Data: 36939-28-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
1-methyl-2-phenylpiperidine is used as a research chemical for studying the effects of psychoactive substances on the central nervous system. Its synthesis and properties provide insights into the development of new drugs and understanding the mechanisms of action of stimulants and hallucinogens.
Used in Toxicological Studies:
MPPP is used as a model compound in toxicological research to investigate the neurotoxic effects of designer drugs and their potential for addiction. This helps in developing strategies for prevention, treatment, and management of substance abuse and related health issues.
Used in Drug Control and Regulation:
As a controlled substance, 1-methyl-2-phenylpiperidine is used in the development and enforcement of drug control policies and regulations. Its identification and monitoring contribute to the prevention of illegal drug trafficking and abuse.

InChI:InChI=1/C12H17N/c1-13-10-6-5-9-12(13)11-7-3-2-4-8-11/h2-4,7-8,12H,5-6,9-10H2,1H3

Upstream product

• 52806-02-7 iodure de 1-methyl-2-phenylpyridinium 
• 32246-12-1 1-Methyl-2-oxo-6-phenyl-piperidin 
• 931-20-4 1-methylpiperidin-2-one 
• 591-51-5 phenyllithium 
• 122333-70-4 cis-N-Methyl-5-phenyl-4-penten-1-amine 
• 122333-64-6 trans-N-Methyl-5-phenyl-4-penten-1-amine 
• 88013-89-2 1-methyl-2-phenyl-1-piperideinium chloride 
• 50-00-0 formaldehyd 
• 3466-80-6 2-phenylpiperidine 
• 117309-97-4 5-Benzenesulfonyl-1-methyl-6-phenyl-piperidin-2-one 
• 17105-71-4 N-methyl-N-benzylformamide 
• 6343-54-0 N-benzylformamide 
• 104936-74-5 N-Benzyl-N'-tert-butyl-N-methyl-formamidine 
• 22768-07-6 (E)-ethyl 5-phenylpent-4-enoate 

Downstream Products

• 3358-68-7 2-Methyl-7-phenyl-hexahydro-1,2-oxazepin 
• 122333-70-4 cis-N-Methyl-5-phenyl-4-penten-1-amine 

Relevant articles and documents

Catalytic methylation of C-H bonds using CO2 and H2

Formation of C-C bonds from CO2 is a much sought after reaction in organic synthesis. To date, other than C-H carboxylations using stoichiometric amounts of metals, base, or organometallic reagents, little is known about C-C bond formation. In fact, to the best of our knowledge no catalytic methylation of C-H bonds using CO2 and H2 has been reported. Described herein is the combination of CO2 and H2 for efficient methylation of carbon nucleophiles such as indoles, pyrroles, and electron-rich arenes. Comparison experiments which employ paraformaldehyde show similar reactivity for the CO2/H2 system. Capturing: Carbon dioxide in the presence of H2 is shown to be an efficient methylating reagent for carbon nucleophiles such as 2-substituted indoles, pyrroles, and electron-rich arenes. Experimental data support the formal capture of formaldehyde. acac=acetylacetonate, triphos=1,1,1-tris(diphenylphosphinomethyl)ethane.

A chemo-enzymatic route to enantiomerically pure cyclic tertiary amines

Deracemization of racemic chiral tertiary amines has been achieved by combination of an enantioselective amine oxidase, obtained through directed evolution, and ammonia borane in a one-pot process. Copyright

Photophysical and photochemical behavior of intramolecular-styrene-amine exciplexes

The photophysical and photochemical behavior of a series of secondary and tertiary ω-(β-styryl)aminoalkanes with one to five methylenes separating the styryl and amino groups has been investigated and compared to the intermolecular reactions of 1-phenylpropene with secondary and tertiary amines. The tertiary styrylamines form fluorescent intramolecular exciplexes, but fail to undergo intramolecular addition reactions. Both the rate constant for exciplex formation and the stability of the exciplex are dependent upon the length of the polymethylene chain connecting the chromophores. The failure of the tertiary amine exciplexes to undergo intramolecular addition is attributed to an unfavorable exciplex geometry for α-C-H transfer to the styrene double bond. While the secondary styrylamines do not form fluorescent exciplexes, the dependence of the styrene singlet lifetime upon the polymethylene chain length is similar to that for the tertiary styrylamines. Intramolecular N-H addition to the styrene double bond results in the formation of two regioisomeric (α-phenyl and α-benzyl) cyclic amines of different ring size. The regioisomer of larger ring size is favored except in the case in which four methylenes separate the chromophores. The effects of polymethylene chain length, solvent polarity, temperature, and the bulk of the N-alkyl group upon product yields and ratios are discussed in terms of a mechanism involving singlet exciplex and biradical intermediates.

INTRAMOLECULAR PHOTOCHEMICAL REACTIONS OF N-ALKYL-5-PHENYL-4-PENTEN-1-AMINES

Irradiation of N-alkyl-5-phenyl-4-penten-1-amines results in the formation of intramolecular styrene-amine adducts and disproportionation products.Increasing the bulk of the N-alkyl group increases the regioselectivity of N-H transfer favoring the formation of piperidine vs. pyrrolidine products and favors disproportionation vs. cyclization.

Remote Dianions. 3. Novel Synthesis of Substituted 2-Piperidones from Imines

The dianion of 4-(phenylsulfonyl)butanoic acid reacts with imines activated by boron trifluoride etherate to afford, after cyclization, substituted 2-piperidones.

STUDY OF CHIROPTICAL PROPERTIES OF SOME PIPERIDINE DERIVATIVES

Chiroptical properties of (S)-(-)-1-methyl-2-phenylpiperidine and (S)-(-)-1-methyl-2-(2-tolyl)-piperidine have been studied.The preferred conformations have been calculated in gradient way on the basis of the CNDO/2 method, and the rotational forces have been calculated for them by direct procedure using the CNDO/S-CI wave function.For comparison of theory and experiment, molar fractions of the individual conformers have been calculated and used together with the rotational forces for construction of the CD spectrum which has been compared with the experimental CD spectrum.Absolute configurations of the mentioned compounds have been determined by chemical correlation.

Lithium Methylorganocuprates Containing Chiral 2-(N-Methyl-2-pyrrolidinyl)-, 2-(N-Methyl-2-piperidinyl)- or 2-(1-N,N-Dimethylaminoethyl)-phenyl Groups. A Comparison of Addition to Two Acyclic Enones

Conjugate addition of the title cuprates to 4-phenyl-3-buten-2-one or 5-phenyl-2,2-dimethyl-4-penten-3-one at -35 deg C gave 4-phenyl-2-pentanone or 5-phenyl-2,2-dimethyl-3-hexanone, respectively, in high chemical yields (80-98percent).The enantiomeric excess, however, was only of the order of 1percent.Both enantiomers of N-methyl-2-phenylpyrrolidine and of N-methyl-2-phenylpiperidine were obtained by resolution with R,R-(+)-tartaric acid and R,R-(-)-O,O-dibenzoyltatraric acid, respectively.