Dropropizine

Base Information

• Chemical Name: Dropropizine
• CAS No.: 17692-31-8
• Deprecated CAS: 117067-01-3
• Molecular Formula: C13H20N2O2
• Molecular Weight: 236.314
• Hs Code.: 2933599090
• European Community (EC) Number: 241-683-7
• NSC Number: 757820
• UNII: U0K8WHL37U
• DSSTox Substance ID: DTXSID0045624
• Nikkaji Number: J10.152D
• Wikipedia: Dropropizine
• Wikidata: Q910111
• NCI Thesaurus Code: C73179
• Metabolomics Workbench ID: 154565
• ChEMBL ID: CHEMBL151445
• Mol file: 17692-31-8.mol

Synonyms:DF 526;DF-526;dipropizine;dipropizine, (S)-isomer;Ditustat;dropropizine;levodropropizine;Levotuss;Tautoss;Zyplo

Chemical Property of Dropropizine

Chemical Property:

• Appearance/Colour: white or almost white powder
• Vapor Pressure: 1.5E-07mmHg at 25°C
• Melting Point: 105-108oC
• Refractive Index: 1.576
• Boiling Point: 412.7 °C at 760 mmHg
• PKA: 14.21±0.20(Predicted)
• Flash Point: 220.9 °C
• PSA: 46.94000
• Density: 1.168 g/cm³
• LogP: 0.16470
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 236.152477885
• Heavy Atom Count: 17
• Complexity: 212

Purity/Quality:

99% ^*data from raw suppliers

racDropropizine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CN(CCN1CC(CO)O)C2=CC=CC=C2
• Recent ClinicalTrials: Evaluation of Efficacy and Safety in Control Cough and the Relief of Nasal Symptoms in Children 2-12 Years Old,Suffering From Cough and Acute Rhinitis
• Uses: antitussive Dropropizine is a cough suppressant and central sedative therapeutic agent.
• Therapeutic Function: Antitussive

Technology Process of Dropropizine

There total 6 articles about Dropropizine 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: 95.0%

C14H18N2O3 → dropropizine (17692-31-8,99291-24-4)

Guidance literature:

With sodium hydroxide; In water; at 23 ℃; for 3h;

DOI:10.1002/cssc.202002267

Reference yield:

active charcoal + S(-)-1,2-(2-propylidene)-3-(4-phenyl-piperazin-1-yl)-propane-1,2-diol + S(-)-1,2-cyclopentylidene)-3-(4-phenyl-piperazin-1-yl)-propane-1,2-diol + (-) 3-(4-phenyl-piperazin-1-yl)-propanediol + (-) 3-(4-phenyl-piperazin-1-yl)-propanediol hydrochloride + S(-)-1,2-cyclohexylidene-3-(4-phenyl-piperazin-1-yl)propane-1,2-diol → dropropizine (17692-31-8,99291-24-4)

Guidance literature:

With ammonium hydroxide; In hydrogenchloride; water;

Reference yield:

(R,S)-3-(4-phenyl-1-piperazinyl)-1,2-propanediol diacetate (142730-57-2) → Acetic acid 2-hydroxy-3-(4-phenyl-piperazin-1-yl)-propyl ester (142730-59-4) + Acetic acid 1-hydroxymethyl-2-(4-phenyl-piperazin-1-yl)-ethyl ester (142730-58-3) + dropropizine (17692-31-8,99291-24-4)

Guidance literature:

With water; at 30 ℃; Lipase Amano PS from Pseudomonas cepacia, 0.5 M phosphate buffer pH 7;

DOI:10.1016/S0040-4039(00)79859-5

upstream raw materials:

(R,S)-3-(4-phenyl-1-piperazinyl)-1,2-propanediol diacetate

4-phenyl-1-piperazine

1-(1-phenyl-4-piperazino)-2,3-epoxypropane

Downstream raw materials:

Acetic acid 2-hydroxy-3-(4-phenyl-piperazin-1-yl)-propyl ester

C₁₃H₂₀N₂O₄

Dropropizin-4-methyliodid

Acetic acid (S)-1-acetoxymethyl-2-(4-phenyl-piperazin-1-yl)-ethyl ester

Refernces

• 1、 -. "1,3-dioxolanes with antitussive activity". . . Retrieved 2008/06/13.
• 2、 Bianchi,Bosetti,Cesti,Golini. "Enzymatic resolution of 1,2-diols: Preparation of optically pure dropropizine". . p. 3231 - 3234. Retrieved 2007/10/02.