3-[1-(Trideuteriomethyl)pyrrolidin-2-yl]pyridine

Base Information

• Chemical Name: 3-[1-(Trideuteriomethyl)pyrrolidin-2-yl]pyridine
• CAS No.: 69980-24-1
• Molecular Formula: C₁₀H₁₄N₂
• Molecular Weight: 165.211
• European Community (EC) Number: 689-510-8
• DSSTox Substance ID: DTXSID80442666
• Nikkaji Number: J1.016.152E
• Mol file: 69980-24-1.mol

Synonyms:69980-24-1;rac-Nicotine-d3;DL-Nicotine-d3;3-[1-(Trideuteriomethyl)pyrrolidin-2-yl]pyridine;DL-Nicotine-(methyl-d3);nicotine-d3;(+/-)-Nicotine-d3 (N-methyl-d3);(+/-)-Nicotine-methyl-d3;Nicotine D3;Nicotine-methyl-d3;?(+/-)-Nicotine-d3;DTXSID80442666;SNICXCGAKADSCV-FIBGUPNXSA-N;()-Nicotine-d3 (N-methyl-d3);CS-O-06811;1-Methyl-d3-2-(3-pyridyl)-pyrrolidine;DL-Nicotine-(methyl-d3), 99 atom % D;3-[1-(?H?)methylpyrrolidin-2-yl]pyridine;D98835;A935320;Pyridine,3-[1-(methyl-d3)-2-pyrrolidinyl]-(9ci)

Chemical Property of 3-[1-(Trideuteriomethyl)pyrrolidin-2-yl]pyridine

Chemical Property:

• Appearance/Colour: clear colourless oil
• Vapor Pressure: 0.03mmHg at 25°C
• Refractive Index: n20/D 1.5265(lit.)
• Boiling Point: 244.447 °C at 760 mmHg
• Flash Point: 101.667 °C
• PSA: 16.13000
• Density: 1.051 g/cm³
• LogP: 1.78620
• Storage Temp.: Refrigerator
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 165.134528693
• Heavy Atom Count: 12
• Complexity: 147

Purity/Quality:

98%,99%, ^*data from raw suppliers

rac-Nicotine-d3 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+
• Hazard Codes: T+,N
• Statements: 26/27/28-36/37/38-63-51/53-27-25
• Safety Statements: 45-61-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCCC1C2=CN=CC=C2
• Isomeric SMILES: [2H]C([2H])([2H])N1CCCC1C2=CN=CC=C2
• Uses: (+/-)-Nicotine-methyl-d3, Labelled rac-Nicotine (N412420). 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 tract and intact skin. Nicotine is used in the treatment of smoking withdrawal syndrome. Nicotine has been used as an anthelmintic. Used for treatment of smoking withdrawal syndrome

Technology Process of 3-[1-(Trideuteriomethyl)pyrrolidin-2-yl]pyridine

There total 2 articles about 3-[1-(Trideuteriomethyl)pyrrolidin-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: 91.0%

iodomethane-d3 (865-50-9) + rac-nornicotine (5746-86-1,13450-58-3) → rac-N-[methyl-d3]nicotine (69980-24-1)

Guidance literature:

rac-nornicotine; With n-butyllithium; In tetrahydrofuran; at -70 ℃; for 0.25h;

iodomethane-d3; at -70 - 0 ℃;

DOI:10.1002/(SICI)1099-1344(199812)41:12<1165::AID-JLCR162>3.0.CO;2-G

Reference yield:

→ rac-N-[methyl-d3]nicotine (69980-24-1)

Guidance literature:

N-Ethoxycarbonylnornicotin (9), LiAlH4 (und Hydrolyse);

DOI:10.1002/jlcr.2580140618

Reference yield:

rac-N-[methyl-d3]nicotine (69980-24-1) → (E)-N-[methyl-d3]-4-(3-pyridinyl)-3-buten-1-amine (220088-40-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / CH₂Cl₂ / 4 h / Heating

2: 77 percent / 0.5 Torr / Heating

3: 84 percent / aq. HCl / 20 h / Heating

With hydrogenchloride; In dichloromethane; 1: Ring cleavage / 2: Dehydrochlorination / 3: Hydrolysis;

DOI:10.1002/(SICI)1099-1344(199812)41:12<1165::AID-JLCR162>3.0.CO;2-G

upstream raw materials:

iodomethane-d3

rac-nornicotine

Downstream raw materials:

(E)-N-[methyl-d3]-4-(3-pyridinyl)-3-buten-1-amine

Refernces

• 1、 Crooks, Peter A.,Ravard, Alain,Byrd, Gary D.. "Synthesis of (E)-N-[methyl-d3]- 4-(3-pyridinyl)-3-buten-1-amine, a deuterated analogue of the nicotinic agonist RJR-2403". . p. 1165 - 1171. Retrieved 2007/10/03.