1-Methyl-4-(3-methoxyphenyl)-1,2,3,6-tetrahydropyridine

Base Information

• Chemical Name: 1-Methyl-4-(3-methoxyphenyl)-1,2,3,6-tetrahydropyridine
• CAS No.: 73224-22-3
• Molecular Formula: C13H17 N O
• Molecular Weight: 203.284
• DSSTox Substance ID: DTXSID50223464
• Nikkaji Number: J518.609I
• Wikidata: Q83101909
• ChEMBL ID: CHEMBL36377
• Mol file: 73224-22-3.mol

Synonyms:1-methyl-4-(3-methoxyphenyl)-1,2,3,6-tetrahydropyridine;m-methoxy-MPTP

Chemical Property of 1-Methyl-4-(3-methoxyphenyl)-1,2,3,6-tetrahydropyridine

Chemical Property:

• Vapor Pressure: 0.000417mmHg at 25°C
• Boiling Point: 316.2°C at 760 mmHg
• Flash Point: 93.4°C
• PSA: 12.47000
• Density: 1.031g/cm³
• LogP: 2.35200
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 203.131014166
• Heavy Atom Count: 15
• Complexity: 237

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC(=CC1)C2=CC(=CC=C2)OC

Technology Process of 1-Methyl-4-(3-methoxyphenyl)-1,2,3,6-tetrahydropyridine

There total 4 articles about 1-Methyl-4-(3-methoxyphenyl)-1,2,3,6-tetrahydropyridine 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: 82.0%

(+/-)-4-(3-methoxyphenyl)-1-methyl-4-piperidinol (73224-20-1) → 1-methyl-4-(3-methoxyphenyl)-1,2,3,6-tetrahydropyridine (73224-22-3)

Guidance literature:

With phosphoric acid; at 70 - 80 ℃; for 3h;

DOI:10.1021/jm00158a033

Reference yield:

phosphorus pentaoxide (337913-25-4) + 1-methyl-4-hydroxy-4-(3-hydroxyphenyl)piperidine (73224-21-2) → 1-methyl-4-(3-methoxyphenyl)-1,2,3,6-tetrahydropyridine (73224-22-3)

Guidance literature:

With ammonium hydroxide; In methanesulfonic acid;

Reference yield:

1-Methyl-4-piperidone (1445-73-4) → 1-methyl-4-(3-methoxyphenyl)-1,2,3,6-tetrahydropyridine (73224-22-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) n-butyllithium / 1.) THF, -78 deg C, 30 min, 2.) THF, -20 deg C, 2 h

2: 82 percent / 85percent aq. phosphoric acid / 3 h / 70 - 80 °C

With n-butyllithium; phosphoric acid;

DOI:10.1021/jm00158a033

upstream raw materials:

(+/-)-4-(3-methoxyphenyl)-1-methyl-4-piperidinol

1-Methyl-4-piperidone

3-methoxyphenyl bromide

phosphorus pentaoxide

Downstream raw materials:

5-(3-methoxyphenyl)-8-methyl-2-oxa-8-azabicyclo<3.3.1>nonane

4-(2-Chloro-ethoxymethyl)-4-(3-methoxy-phenyl)-1-methyl-1,2,3,4-tetrahydro-pyridine

4-(2-Chloro-propoxymethyl)-4-(3-methoxy-phenyl)-1-methyl-1,2,3,4-tetrahydro-pyridine

picenadol

Refernces

Synthesis, antinociceptive activity and opioid receptor profiles of 3-(0ctahydro-1H-pyrano- And -thiopyrano[4,3-c]pyridin-8a-yl)phenols

10.1039/P19890001177

The research aims to synthesize and evaluate a series of novel cis- and trans-3-(octahydro-1H-pyrano[4,3-c]pyridin-8a-yl)phenols and related thiopyrano systems for their antinociceptive activity and opioid receptor profiles. The study employs alkylation and hydrogenation techniques to generate these compounds. 1-methyl-4-(3-methoxyphenyl)-1,2,3,6-tetrahydropyridine (7) serves as the foundational starting material, while 2-chloro-1-(chloromethoxy)ethane acts as a key alkylating agent. Together, they enable the synthesis of the intermediate enamine (8a) and the subsequent formation of the bicyclic enamine (9a), which are essential steps in the construction of the target compounds. The synthesized compounds are then tested in vivo using the mouse acetylcholine-induced abdominal constriction test and the rat urine output model, and in vitro using the guinea-pig ileum and rabbit vas deferens preparations. The results show that certain derivatives, like (13l) and (21c), exhibit high potency and selective K-agonist profiles, indicating their potential as safer analgesics compared to traditional morphine-like drugs. The study concludes that the combination of new in vivo and in vitro test systems effectively distinguishes between μ- and K-agonists, providing valuable insights into the structure-activity relationships of these novel compounds.

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