Rotigotine hydrochloride

Base Information

• Chemical Name: Rotigotine hydrochloride
• CAS No.: 125572-93-2
• Molecular Formula: C19H25NOS^.HCl
• Molecular Weight: 351.941
• Hs Code.: 2934990002
• European Community (EC) Number: 603-080-0
• UNII: 6Q1W9573L2
• DSSTox Substance ID: DTXSID80154792
• Wikidata: Q27265316
• Mol file: 125572-93-2.mol

Synonyms:(+)-5,6,7,8-tetrahydro-6-(propyl(2-(2-thienyl)ethyl)amino)-1-naphthol;(+--)-5,6,7,8-tetrahydro-6-(propyl(2-(2-thienyl)ethyl)amino)-1-naphthol;1-naphthalenol, 5,6,7,8-tetrahydro-6-(propyl(2-(2-thienyl)ethyl)amino)-;2-(N-n-propyl-N-2-thienylethylamino)-5-hydroxytetralin;N 0437;N 0437, (+-)-isomer;N 0437, (-)-isomer;N 0437, (R)-isomer;N 0437, hydrochloride, (R)-isomer;N 0437, hydrochloride, (S)-isomer;N 0923;N 0924;N-0437;N-0923;N-0924;Neupro;racemic N-0437;rotigotine;rotigotine (+-)-form;Rotigotine CDS;rotigotine, (+)-;rotigotine, (+--)-

Chemical Property of Rotigotine hydrochloride

Chemical Property:

• Appearance/Colour: Almost white to white crystalline powder
• Vapor Pressure: 1.84E-09mmHg at 25°C
• Melting Point: 186.5-187.5oC
• Boiling Point: 470.1 °C at 760 mmHg
• Flash Point: 238.1 °C
• PSA: 51.71000
• Density: 1.2g/cm3 at 20℃
• LogP: 5.06770
• Storage Temp.: Desiccate at RT
• Solubility.: Acetone (Slightly, Heated, Sonicated), DMSO (Slightly), Methanol (Slightly)
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 351.1423633
• Heavy Atom Count: 23
• Complexity: 337

Purity/Quality:

99.9% ^*data from raw suppliers

Rotigotine hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCN(CCC1=CC=CS1)C2CCC3=C(C2)C=CC=C3O.Cl
• Isomeric SMILES: CCCN(CCC1=CC=CS1)[C@H]2CCC3=C(C2)C=CC=C3O.Cl
• Recent ClinicalTrials: Treatment of Parkinson's Disease With a Transdermal Skin Patch
• Recent EU Clinical Trials: A randomized, double-blind, placebo-controlled, parallel-group proof-of-concept trial to assess the efficacy, safety and tolerability of ascending doses of rotigotine nasal spray for the acute treatment of RLS symptoms in subjects with idiopathic Restless Legs Syndrome
• Uses: It is a non-ergot dopamine agonist drug and is indicated for the treatment of Parkinson’s disease.

Technology Process of Rotigotine hydrochloride

There total 22 articles about Rotigotine hydrochloride 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: 96.0%

rotigotine (99755-59-6,112835-48-0) → rotigotine hydrochloride (125572-93-2,102120-99-0,125572-92-1)

Guidance literature:

With hydrogenchloride; In methanol; at 20 ℃; for 4h; Inert atmosphere;

DOI:10.1002/adsc.201701198

Reference yield: 82.0%

(2S)-5-methoxy-N-propyl-N-(2'-(thien-2-yl)ethyl)tetralin-2-amine hydrochloride (1232344-37-4) → rotigotine hydrochloride (125572-93-2,102120-99-0,125572-92-1)

Guidance literature:

(2S)-5-methoxy-N-propyl-N-(2'-(thien-2-yl)ethyl)tetralin-2-amine hydrochloride; With aluminum (III) chloride; thiourea; In toluene; at 60 - 65 ℃;

With ammonia; In water; toluene; at 15 - 30 ℃; pH=8 - 9;

With hydrogenchloride; In dichloromethane;

Reference yield: 82.0%

2-(2-thienyl)ethyl tosylate (40412-06-4) + (S)-1,2,3,4-tetrahydro-5-hydroxy-N-propyl-naphthalen-2-ammonium hydrobromide (165950-84-5,167016-87-7) → rotigotine hydrochloride (125572-93-2,102120-99-0,125572-92-1)

Guidance literature:

(S)-1,2,3,4-tetrahydro-5-hydroxy-N-propyl-naphthalen-2-ammonium hydrobromide; With sodium carbonate; In o-xylene; water; at 70 - 80 ℃;

2-(2-thienyl)ethyl tosylate; With sodium carbonate; In o-xylene; Reflux;

With hydrogenchloride; In o-xylene; water; isopropyl alcohol; toluene; at 15 - 55 ℃;

upstream raw materials:

rotigotine

(2S)-5-methoxy-N-propyl-N-(2'-(thien-2-yl)ethyl)tetralin-2-amine

(2S)-5-methoxy-N-propyl-N-(2'-(thien-2-yl)ethyl)tetralin-2-amine hydrochloride

(S)-(5-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propylamine hydrochloride

Downstream raw materials:

rotigotine

Refernces

• 1、 Park, Do Young,Kim, Kyung-Hee,Cheon, Cheol-Hong. "Enantioselective Synthesis of β-Aminotetralins via Chiral Phosphoric Acid-catalyzed Reductive Amination of β-Tetralones". supporting information. p. 462 - 467. Retrieved 2017/12/07.
• 2、 -. "S-5-SUBSTITUENT-N-2'-(THIOPHENE-2-YL)ETHYL-TETRALIN-2-AMINE OR CHIRAL ACID SALTS THEREOF AND USE FOR PREPARING ROTIGOTINE". Paragraph 0055. . Retrieved 2013/03/26.