DIMETHYL-(6-METHYL-2-P-TOLYL-IMIDAZO[1,2-A]PYRIDIN-3-YLMETHYL)-AMINE

Base Information

• Chemical Name: DIMETHYL-(6-METHYL-2-P-TOLYL-IMIDAZO[1,2-A]PYRIDIN-3-YLMETHYL)-AMINE
• CAS No.: 106961-33-5
• Molecular Formula: C18H21 N3
• Molecular Weight: 279.385
• Hs Code.: 2933990090
• Mol file: 106961-33-5.mol

Synonyms:3-(Dimethylaminomethyl)-6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridine

Chemical Property of DIMETHYL-(6-METHYL-2-P-TOLYL-IMIDAZO[1,2-A]PYRIDIN-3-YLMETHYL)-AMINE

Chemical Property:

• PKA: 8.30±0.28(Predicted)
• PSA: 20.54000
• Density: 1.07±0.1 g/cm3(Predicted)
• LogP: 3.67970
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

99%min ^*data from raw suppliers

3-(Dimethylaminomethyl)-6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 3-(Dimethylaminomethyl)-6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridine is an impurity of Zolpidem (Z650000), a selective non-benzodiazepine GABAA receptor agonist.

Technology Process of DIMETHYL-(6-METHYL-2-P-TOLYL-IMIDAZO[1,2-A]PYRIDIN-3-YLMETHYL)-AMINE

There total 4 articles about DIMETHYL-(6-METHYL-2-P-TOLYL-IMIDAZO[1,2-A]PYRIDIN-3-YLMETHYL)-AMINE 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: 91.6%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 6-methyl-2-(4-methyl-phenyl)-imidazo[1,2-a]pyridine (88965-00-8) + dimethyl amine (124-40-3) → dimethyl-(6-methyl-2-p-tolylimidazo[1,2-a]pyridin-3-ylmethyl)-amine (106961-33-5)

Guidance literature:

formaldehyd; 6-methyl-2-(4-methyl-phenyl)-imidazo[1,2-a]pyridine; dimethyl amine; With acetic acid; In water; at 0 - 55 ℃; for 3 - 4h;

With sodium hydroxide; water; pH=8 - 8.5; Product distribution / selectivity;

Reference yield: 82.0%

dimethyl amine (124-40-3) + (6-methyl-2-(p-tolyl)imidazo[1,2-a]pyridin-3-yl)methanol (887282-93-1) → dimethyl-(6-methyl-2-p-tolylimidazo[1,2-a]pyridin-3-ylmethyl)-amine (106961-33-5)

Guidance literature:

(6-methyl-2-(p-tolyl)imidazo[1,2-a]pyridin-3-yl)methanol; With thionyl chloride; In dichloromethane; at 20 - 25 ℃; for 6h; Schlenk technique;

dimethyl amine; In acetonitrile; at 20 - 25 ℃; for 18h; Reagent/catalyst; Solvent; Temperature; Schlenk technique;

DOI:10.1002/anie.202104503

Reference yield:

6-methyl-2-(4-methyl-phenyl)-imidazo[1,2-a]pyridine (88965-00-8) → dimethyl-(6-methyl-2-p-tolylimidazo[1,2-a]pyridin-3-ylmethyl)-amine (106961-33-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium metaperiodate / water / 24 h / 90 °C / Schlenk technique

2.1: thionyl chloride / dichloromethane / 6 h / 20 - 25 °C / Schlenk technique

2.2: 18 h / 20 - 25 °C / Schlenk technique

With thionyl chloride; potassium metaperiodate; In dichloromethane; water;

DOI:10.1002/anie.202104503

upstream raw materials:

formaldehyd

6-methyl-2-(4-methyl-phenyl)-imidazo[1,2-a]pyridine

dimethyl amine

(6-methyl-2-(p-tolyl)imidazo[1,2-a]pyridin-3-yl)methanol

Downstream raw materials:

Trimethyl-(6-methyl-2-p-tolyl-imidazo[1,2-a]pyridin-3-ylmethyl)-ammonium; iodide

6-methyl-3-cyanomethyl-2-(4-methylphenyl)imidazo[1,2-a]pyridine

2-(4-methylphenyl)-6-methylimidazo[1,2-α]pyridine-3-acetamide

6-methyl-2-(4-methylphenyl)-imidazo<1,2-a>pyridine-3-acetic acid

Refernces

• 1、 -. "2-ARYL IMIDAZO[1,2-A]PYRIDINE-3-ACETAMIDE DERIVATIVES, PREPARATION METHODS AND USE THEREOF". Paragraph 0053. . Retrieved 2013/05/09.
• 2、 -. "PROCESS FOR PREPARING ZOLPIDEM". Page/Page column title page; sheet 1; 6. . Retrieved 2010/11/25.