99291-25-5

Basic information

• Product Name: Levodropropizine
• Synonyms: (S)-3-(4-Phenyl-1-piperazinyl)-1,2-propanediol;Levodropropizine;(2S)-3-(4-Phenyl-1-piperazinyl)-1,2-propanediol;Danka;l-Dropropizine;Levotuss;LVDP;Rapitux
• CAS NO: 99291-25-5
• Molecular Formula: C₁₃H₂₀N₂O₂
• Molecular Weight: 236.31
• EINECS: 1592732-453-0
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;raw materials
• Mol File: 99291-25-5.mol
• Article Data: 8

Chemical Properties

• Melting Point: 98-100°C
• Boiling Point: 412.7 °C at 760 mmHg
• Flash Point: 220.9 °C
• Appearance: white solid
• Density: 1.168 g/cm³
• Vapor Pressure: 1.5E-07mmHg at 25°C
• Refractive Index: 1.576
• Storage Temp.: Refrigerator
• Solubility: Slightly soluble in water, freely soluble in dilute acetic acid and in methanol, slightly soluble in ethanol (96 per cent).
• PKA: 14.21±0.20(Predicted)
• CAS DataBase Reference: Levodropropizine(CAS DataBase Reference)
• NIST Chemistry Reference: Levodropropizine(99291-25-5)
• EPA Substance Registry System: Levodropropizine(99291-25-5)

Safety Data

• Hazardous Substances Data: 99291-25-5(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 99291-25-5 differently. You can refer to the following data:
1. S-Form of Dropropizine. Cough suppressive phenylpiperazine derivative. Antitussive
2. Cough Suppressant
3. S-Form of Dropropizine. Cough suppressive phenylpiperazine derivative. Antitussive.

Definition

ChEBI: A member of the class of N-arylpiperazines that is N-phenylpiperazine in which the amino hydrogen is replaced by a 2,3-dihydroxypropyl group (the S-enantiomer). A peripherally acting antitussive drug t at is used as an alternative to opioids.

InChI:InChI=1/C13H20N2O2/c16-11-13(17)10-14-6-8-15(9-7-14)12-4-2-1-3-5-12/h1-5,13,16-17H,6-11H2/t13-/m0/s1

Upstream product

• 92-54-6 4-phenyl-1-piperazine 
• 57090-45-6 (2R)-3-chloro-1,2-propanediol 
• 113826-06-5 (R)-glycidyl tosylate 
• 50765-70-3 (S)-1-tosyloxy-2,3-propanediol 

Relevant articles and documents

Catalytic, Kinetic, and Mechanistic Insights into the Fixation of CO2 with Epoxides Catalyzed by Phenol-Functionalized Phosphonium Salts

A series of hydroxy-functionalized phosphonium salts were studied as bifunctional catalysts for the conversion of CO2 with epoxides under mild and solvent-free conditions. The reaction in the presence of a phenol-based phosphonium iodide proceeded via a first order rection kinetic with respect to the substrate. Notably, in contrast to the aliphatic analogue, the phenol-based catalyst showed no product inhibition. The temperature dependence of the reaction rate was investigated, and the activation energy for the model reaction was determined from an Arrhenius-plot (Ea=39.6 kJ mol?1). The substrate scope was also evaluated. Under the optimized reaction conditions, 20 terminal epoxides were converted at room temperature to the corresponding cyclic carbonates, which were isolated in yields up to 99 %. The reaction is easily scalable and was performed on a scale up to 50 g substrate. Moreover, this method was applied in the synthesis of the antitussive agent dropropizine starting from epichlorohydrin and phenylpiperazine. Furthermore, DFT calculations were performed to rationalize the mechanism and the high efficiency of the phenol-based phosphonium iodide catalyst. The calculation confirmed the activation of the epoxide via hydrogen bonding for the iodide salt, which facilitates the ring-opening step. Notably, the effective Gibbs energy barrier regarding this step is 97 kJ mol?1 for the bromide and 72 kJ mol?1 for the iodide salt, which explains the difference in activity.

Chemo-enzymatic synthesis of levodropropizine

Levodropropizine, an antitussive drug, was prepared in high enantiomeric excess in three steps, starting from dichloroacetone (2). Monosubstitution of 2 with sodium benzoate and subsequent baker's yeast reduction stereoselectively afforded the corresponding chlorohydrin in 73% ee, which was converted to levodropropizine and enantiomerically enriched up to 95% ee by fractional crystallisation.

A process for the optical resolution of dropropizine

A process for the optical resolution of racemic dropropizine, carried out using L(+)tartaric acid as the optical resolution agent in aqueous medium, is described.