5-Methyl-2-(1-methylpyrrolidin-2-yl)pyridine

Base Information

• Chemical Name: 5-Methyl-2-(1-methylpyrrolidin-2-yl)pyridine
• CAS No.: 101540-79-8
• Molecular Formula: C₁₁H₁₆N₂
• Molecular Weight: 176.261
• DSSTox Substance ID: DTXSID70699006
• Mol file: 101540-79-8.mol

Synonyms:5-methyl-2-(1-methylpyrrolidin-2-yl)pyridine;3-METHYL-6-(1-METHYL-2-PYRROLIDINYL)PYRIDINE;SCHEMBL17888372;DTXSID70699006;AKOS030255812

Chemical Property of 5-Methyl-2-(1-methylpyrrolidin-2-yl)pyridine

Chemical Property:

• Melting Point: Yellow Liquid
• PSA: 16.13000
• LogP: 2.09460
• Storage Temp.: -20°C Freezer
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 176.131348519
• Heavy Atom Count: 13
• Complexity: 170

Purity/Quality:

98%min ^*data from raw suppliers

(+/-)-6-Methylnicotine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CN=C(C=C1)C2CCCN2C
• Uses: A metabolite of Nicotine

Technology Process of 5-Methyl-2-(1-methylpyrrolidin-2-yl)pyridine

There total 12 articles about 5-Methyl-2-(1-methylpyrrolidin-2-yl)pyridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 81.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 2-methyl-5-(pyrrolidin-2-yl)pyridine (90872-72-3) → (S)-6-Methylnicotine (101540-79-8)

Guidance literature:

With formic acid; for 12h; Heating;

DOI:10.1021/jo00328a010

Reference yield: 25.0%

3-(1-methylpyrrolidin-2-yl)pyridine 1-oxide (23113-16-8) + methylmagnesium bromide (75-16-1) → (S)-6-Methylnicotine (101540-79-8) + 2-methylnicotine (64114-31-4)

Guidance literature:

In tetrahydrofuran; at -70 ℃; Product distribution; var. temp.;

DOI:10.1021/jo00173a023

Reference yield: 22.0%

methyllithium (917-54-4) + 3-(1-methyl-pyrrolidin-2-yl)-pyridine (22083-74-5) → (S)-6-Methylnicotine (101540-79-8) + (+/-)-4-Methylnicotine (65556-02-7) + 2-methylnicotine (64114-31-4)

Guidance literature:

Product distribution; Mechanism; 1.) ether, heat, 1 h, 2.) decalin, 110 deg C, 7 h; var. solvent, var. temp., var. conc.;

DOI:10.1021/jo00173a023

upstream raw materials:

3-(1-methylpyrrolidin-2-yl)pyridine 1-oxide

methylmagnesium bromide

methyllithium

nicotin

Downstream raw materials:

2-[5-(1-methyl-pyrrolidin-2-yl)-pyridin-2-yl]-1-phenyl-ethanol

Refernces

• 1、 Seeman, Jeffrey I.,Secor, Henry V.,Howe, Charles R.,Chavdarian, Charles G.,Morgan, Larry W.. "Organometallic Methylation of Nicotine and Nicotine N-Oxide. Rection Pathways and Racemization Mechanisms". . p. 4899 - 4904. Retrieved 2007/10/02.
• 2、 Seeman, Jeffrey I.,Secor, Henry V.,Chavdarian, Charles G.,Sanders, Edward B.,Bassfield, Ronald L.,Whidby, Jerry F.. "Steric and Conformational Effects in Nicotine Chemistry". . p. 3040 - 3048. Retrieved 2007/10/02.