Didesmethylchlorpheniramine

Base Information

• Chemical Name: Didesmethylchlorpheniramine
• CAS No.: 20619-13-0
• Molecular Formula: C14H15 Cl N2
• Molecular Weight: 246.739
• UNII: WW1P1ER09X
• DSSTox Substance ID: DTXSID90942804
• Nikkaji Number: J390.523C
• Wikidata: Q27292942
• Mol file: 20619-13-0.mol

Synonyms:DDCP;N,N-didemethylchlorpheniramine;N,N-didemethylchlorpheniramine, (S)-isomer

Chemical Property of Didesmethylchlorpheniramine

Chemical Property:

• Vapor Pressure: 8.6E-06mmHg at 25°C
• Boiling Point: 374°Cat760mmHg
• Flash Point: 180°C
• Density: 1.166g/cm³
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 246.0923762
• Heavy Atom Count: 17
• Complexity: 214

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=NC(=C1)C(CCN)C2=CC=C(C=C2)Cl

Technology Process of Didesmethylchlorpheniramine

There total 14 articles about Didesmethylchlorpheniramine 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: 80.0%

3-(4-chlorophenyl)-3-(pyridin-2-yl)propanenitrile (405551-70-4) → Didesmethylchlorpheniramine (20619-13-0)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; for 12h; Reflux;

DOI:10.1021/acs.orglett.5b01746

Reference yield:

2-(4-chlorobenzyl)pyridine (4350-41-8) + 3-bromopropinaldehyde diethyl acetal (59067-07-1) → Didesmethylchlorpheniramine (20619-13-0)

Guidance literature:

2-(4-chlorobenzyl)pyridine; With sodium amide; In toluene; at 20 ℃; for 0.333333h;

3-bromopropinaldehyde diethyl acetal; In toluene; for 8h; Reflux;

Reference yield:

1-(4-chlorophenyl-1-(2-pyridyl))ehylene (160911-84-2) → Didesmethylchlorpheniramine (20619-13-0)

Guidance literature:

Multi-step reaction with 3 steps

1: copper(II) acetate monohydrate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer / tert-Amyl alcohol / 12 h / 100 °C / Inert atmosphere; Sealed tube

2: sodium tetrahydroborate / isopropyl alcohol / Reflux

3: lithium aluminium tetrahydride / diethyl ether / 12 h / Reflux

With sodium tetrahydroborate; lithium aluminium tetrahydride; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate monohydrate; In tert-Amyl alcohol; diethyl ether; isopropyl alcohol;

DOI:10.1021/acs.orglett.5b01746

upstream raw materials:

2-(4-Chloro-phenyl)-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-pyridin-2-yl-butyronitrile

3-(4-chlorophenyl)-3-(pyridin-2-yl)propanenitrile

2-(4-chlorobenzoyl)pyridine

3-(4-chloro-phenyl)-3-pyridin-2-yl-acrylonitrile

Downstream raw materials:

chlorphenamine maleate

1-[3-(4-chloro-phenyl)-3-pyridin-2-yl-propyl]-3-[4-(1-trityl-1H-imidazol-4-yl)-butyl]-urea

N-[3-(4-chloro-phenyl)-3-pyridin-2-yl-propyl]-N-methyl-3-(1-trityl-1H-imidazol-4-yl)-propionamide

[3-(4-chloro-phenyl)-3-pyridin-2-yl-propyl]-[3-(1-trityl-1H-imidazol-4-yl)-propyl]-amine