3-(1-Methylpyrrolidin-2-yl)pyridine

Base Information

• Chemical Name: 3-(1-Methylpyrrolidin-2-yl)pyridine
• CAS No.: 22083-74-5
• Molecular Formula: C10H14 N2
• Molecular Weight: 162.235
• European Community (EC) Number: 623-834-2
• NSC Number: 5065
• UN Number: 1654
• DSSTox Substance ID: DTXSID3048154
• Nikkaji Number: J23.948H
• Wikidata: Q12144
• Pharos Ligand ID: U94HYPVTTQUG
• Metabolomics Workbench ID: 134051
• ChEMBL ID: CHEMBL440464
• Mol file: 22083-74-5.mol

Synonyms:22083-74-5;3-(1-methylpyrrolidin-2-yl)pyridine;(+/-)-Nicotine;(R,S)-Nicotine;Pyridine, 3-(1-methyl-2-pyrrolidinyl)-;(+-)-Nicotine;Nikotin;DL-Nicotine;(RS)-Nicotine;Nicotine, (+-)-;[3H]NICOTINE;(+/-)-Nicotine-d7;75202-10-7;3-(1-Methyl-2-pyrrolidinyl)pyridine;CHEMBL440464;(+-)-3-(1-Methyl-2-pyrrolidinyl)pyridine;NSC5065;1-Methyl-2-(3-pyridyl)pyrrolidine;3-[1-Methylpyrrolidin-2-yl]pyridine;BRN 0082111;destruxol;1-Methyl-2-(3-pyridyl]pyrrolidine;S-(-)-Nicotine;DL-tetrahydronicotyrine;1219805-86-3;SMR000471862;methyl-2-pyrrolidinyl)pyridine;CHEBI:18723;rac-Nicotine;racemic nicotine;1-methyl-2-(3-pyridal)-pyrrolidene;Flux Maay;Nicotine, liquid;niagara p.a.;Nicotine-(+);Ortho N-4;Ortho N-5;Nicotine (not validated);D02BPT;(+/-)NICOTINE;SCHEMBL20193;MLS001066400;MLS001332491;GTPL3978;XL All Insecti-cide, Emo-Nib;DTXSID3048154;SCHEMBL11976729;CHEBI:138000;US8609708, 54 Nicotine;GLXC-19133;HMS2267D10;HMS3373A19;WLN: T6NJ C- BT5NTJ A1;BBL028104;BDBM50004108;STL146319;1-methyl-2-(3-pyridyl) pyrrolidine;AKOS005720800;AB05474;VS-0124;NCGC00161830-01;BP-13421;LS-96489;.beta.-Pyridyl-.alpha.-N-methylpyrrolidine;(+/-)-Nicotine, >=99% (TLC), liquid;(+/-)-3-(1-Methyl-2-pyrrolidinyl)pyridine;3-(tetrahydro-1-methyl pyrrol-2-yl)Pyridine;EN300-123020;Q12144;AB00919090_06;J-014481;3-(1-METHYL-4,5-DIHYDRO-3H-PYRROL-5-YL)PYRIDINE

Chemical Property of 3-(1-Methylpyrrolidin-2-yl)pyridine

Chemical Property:

• Vapor Pressure: 0.0303mmHg at 25°C
• Melting Point: -79 °C
• Boiling Point: 244.4°Cat760mmHg
• PKA: 8.02(at 25℃)
• Flash Point: 101.7°C
• PSA: 16.13000
• Density: 1.032g/cm³
• LogP: 1.78620
• Storage Temp.: Refrigerator
• Solubility.: ethanol: 50 mg/mL
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 162.115698455
• Heavy Atom Count: 12
• Complexity: 147
• Transport DOT Label: Poison

Purity/Quality:

99.9% ^*data from raw suppliers

rac-Nicotine ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T+,N
• Statements: 25-27-51/53
• Safety Statements: 36/37-45-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN1CCCC1C2=CN=CC=C2
• Recent EU Clinical Trials: A double-blind, randomized, placebo- and NRT-controlled Phase II study to assess the effects of EVT 302 alone and in combination with NRT on craving and withdrawal in healthy male smokers deprived of cigarettes
• Uses: This is the unnatural isomer of Nicotine (+/-)-NICOTINE is an alkaloid isolated from plants. It is an active stimulant, having both addictive and carcinogenic properties. Nicotine is an alkaloid isolated from plants. Nicotine is an active stimulant, having both addictive and carcinogenic properties. Nicotine can be absorbed through the alimentary canal, respiratory tra ct and intact skin. Nicotine is used in the treatment of smoking withdrawal syndrome. Nicotine has been used as an anthelmintic.

Technology Process of 3-(1-Methylpyrrolidin-2-yl)pyridine

There total 88 articles about 3-(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: 99.1%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + formic acid (64-18-6) + rac-nornicotine (5746-86-1,13450-58-3) → 3-(1-methyl-pyrrolidin-2-yl)-pyridine (22083-74-5)

Guidance literature:

formaldehyd; formic acid; rac-nornicotine; In water; at 85 ℃; for 20h;

With sodium hydroxide; In water; pH=13;

Reference yield: 98.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 3-(3,4-dihydro-2H-pyrrol-2-yl)-pyridine (53844-46-5) → 3-(1-methyl-pyrrolidin-2-yl)-pyridine (22083-74-5)

Guidance literature:

With formic acid; In water; at 80 ℃; for 18h;

DOI:10.1021/acs.orglett.8b03909

Reference yield: 96.5%

D-nicotine (25162-00-9) → 3-(1-methyl-pyrrolidin-2-yl)-pyridine (22083-74-5)

Guidance literature:

With 18-crown-6 ether; potassium tert-butylate; at 80 ℃; for 1h; Reagent/catalyst; Temperature; Inert atmosphere;

upstream raw materials:

nicotirine

tetrachloromethane

1-methyl-2-(3-pyridyl)-3-pyrroline

ethylene glycol

Downstream raw materials:

dimethyl-[4-(1-methyl-[3]piperidyl)-butyl]-amine

N-methyl-N-(4-pyridin-3-yl-but-3-enyl)-benzamide

(S)-1-benzyl-3-(1-benzyl-1-methyl-pyrrolidinium-2-yl)-pyridinium; diiodide

3-hydroxy-2-butanon

Refernces

• 1、 Schütte,Stephan. "On the biosynthesis of nicotine". . p. 1355 - 1356. Retrieved 1967.
• 2、 Breuer,Melumad. "A one-step synthesis of nicotine from cyclopropyl 3-pyridyl ketone.". . p. 3595 - 3596. Retrieved 1969.
• 3、 Cai, Bin,Ji, Huihua,Fannin, Franklin F.,Bush, Lowell P.. "Contribution of Nicotine and Nornicotine toward the Production of N′-Nitrosonornicotine in Air-Cured Tobacco (Nicotiana tabacum)". . p. 754 - 759. Retrieved 2016.
• 4、 SUGASAWA,TATSUNO,KAMIYA. "A new synthesis of rac-nicotine.". . p. 39 - 41. Retrieved 1954.
• 5、 -. "Preparation method of nicotine and intermediate thereof". Paragraph 0149-0152. . Retrieved 2021/06/02.
• 6、 -. "Preparation method of artificially synthesized (R, S)-nicotine salt". Paragraph 0050; 0054-0055; 0064-0066; 0070-0072; 0075-0077. . Retrieved 2021/06/02.