Methyl 1,2,5,6-Tetrahydropyridine-3-carboxylate Hydrochloride

Base Information

• Chemical Name: Methyl 1,2,5,6-Tetrahydropyridine-3-carboxylate Hydrochloride
• CAS No.: 6197-39-3
• Molecular Formula: C7H12ClNO2
• Molecular Weight: 177.6287
• Hs Code.: 2933399090
• Mol file: 6197-39-3.mol

Synonyms:Guvacoline hydrochloride;methyl 1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride;Norarecoline hydrochloride;guvacine methyl esther hydrocloride;3-Pyridinecarboxylic acid,1,2,5,6-tetrahydro-,methyl ester,hydrochloride;1,2,5,6-Tetrahydro-3-pyridinecarboxylic acid methyl ester hydrochloride;methyl 1,2,5,6-tetrahydro-3-pyridinecarboxylate hydrochloride;Norarecoline HCl;Guvacine methyl ester hydrochloride;methyl 1,2,3,6-tetrahydropyridine-5-carboxylate hydrochloride;

Chemical Property of Methyl 1,2,5,6-Tetrahydropyridine-3-carboxylate Hydrochloride

Chemical Property:

• Vapor Pressure: 0.207mmHg at 25°C
• Melting Point: 121-122 °C
• Boiling Point: 209.1°Cat760mmHg
• Flash Point: 80.2°C
• PSA: 38.33000
• Density: g/cm³
• LogP: 1.20990
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO

Purity/Quality:

≥98% ^*data from raw suppliers

Methyl1,2,5,6-tetrahydropyridine-3-carboxylatehydrochloride 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Guvacoline Hydrochloride is an intermediate in the synthesis of N-Nitrosoguvacoline (N527625), one of the N-nitrosation products of arecoline. It is the only one N-nitrosamine found in Taiwanese betel quid chewing saliva. It is used as a standard for the determination of Nitrosamine in tobacco smoke.

Technology Process of Methyl 1,2,5,6-Tetrahydropyridine-3-carboxylate Hydrochloride

There total 2 articles about Methyl 1,2,5,6-Tetrahydropyridine-3-carboxylate Hydrochloride 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: 94.0%

arecoline (63-75-2) → 1,2,5,6-tetrahydro-3-pyridinecarboxylic acid methyl ester hydrochloride (6197-39-3)

Guidance literature:

With aluminum oxide; silica gel; potassium carbonate; sodium percarbonate; sodium salt of 2,4-dichloro-6-hydroxy-1,3,5-triazine; In chloroform; column chromatography;

DOI:10.1021/ol036319g

Reference yield:

arecoline hydrobromide (300-08-3) → 1,2,5,6-tetrahydro-3-pyridinecarboxylic acid methyl ester hydrochloride (6197-39-3)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium carbonate / water / pH 13 - 14

2: 1,2-dichloro-ethane; carbonochloridic acid 1-chloro-ethyl ester / dichloromethane / 6.25 h / 0 - 100 °C / pH 13 - 14

With carbonochloridic acid 1-chloro-ethyl ester; sodium carbonate; 1,2-dichloro-ethane; In dichloromethane; water;

DOI:10.1016/j.bmc.2013.07.012

Reference yield:

1,2,5,6-tetrahydro-3-pyridinecarboxylic acid methyl ester hydrochloride (6197-39-3) + benzyl bromide (100-39-0) → 1-benzyl-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester (88928-69-2)

Guidance literature:

With sodium hydrogencarbonate; In ethanol; at 0 - 110 ℃; for 5.08333h;

DOI:10.1016/j.bmc.2013.07.012

upstream raw materials:

arecoline

arecoline hydrobromide

Downstream raw materials:

sodium 1-benzyl-1,2,5,6-tetrahydropyridine-3-carboxylate

1-benzyl-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester

Refernces

• 1、 -. "Beta-sulfonamide hydroxamic acid inhibitors of tace/matrix metalloproteinase". Page/Page column 38-39. . Retrieved 2008/06/13.
• 2、 Olofson, R. A.,Martz, Jonathan T.,Senet, Jean-Pierre,Piteau, Marc,Malfroot, Thierry. "A New Reagent for the Selective, High-Yield N-Dealkylation of Tertiary Amines: Improved Syntheses of Naltrexone and Nalbuphine". . p. 2081 - 2082. Retrieved 2007/10/02.