102120-99-0

Basic information

• Product Name: rac-Rotigotine Hydrochloride
• Synonyms: rac-Rotigotine Hydrochloride;5,6,7,8-Tetrahydro-6-[propyl[2-(2-thienyl)ethyl]aMino]-1-naphthalenol Hydrochloride;1-Naphthalenol, 5,6,7,8-tetrahydro-6-[propyl[2-(2-thienyl)ethyl]aMino]-, (Hydrochloride) (1:1);1-Naphthalenol,5,6,7,8-tetrahydro-6-[propyl[2-(2-thienyl)ethyl]amino]-,hydrochloride;N 0437 hydrochloride
• CAS NO: 102120-99-0
• Molecular Formula: C19H26ClNOS
• Molecular Weight: 351.93384
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 102120-99-0.mol
• Article Data: 14

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: Acetone, DMSO, Methanol
• CAS DataBase Reference: rac-Rotigotine Hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: rac-Rotigotine Hydrochloride(102120-99-0)
• EPA Substance Registry System: rac-Rotigotine Hydrochloride(102120-99-0)

Safety Data

• Hazardous Substances Data: 102120-99-0(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Racemic mixture of Rotigotine and ent-Rotigotine

Upstream product

• 112835-48-0 (-)-2-(N-propyl-N-2-thienylethylamino)5-hydroxytetralin 
• 39098-97-0 2-thienylacetic acid chloride 
• 32940-15-1 5-methoxy-2-tetralone 
• 1918-77-0 Thiophene-2-acetic acid 
• 165950-84-5 (S)-1,2,3,4-tetrahydro-5-hydroxy-N-propyl-naphthalen-2-ammonium hydrobromide 
• 3904-24-3 (5-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propylamine hydrochloride 
• 101403-25-2 (R)-1,2,3,4-tetrahydro-5-methoxy-N-propyl-naphthalen-2-amine 
• 1352917-68-0 (S)-1,2,3,4-tetrahydro-5-methoxy-N-propyl-naphthalen-2-ammonium (S)-2-methoxy-2-phenylacetate 
• 93601-86-6 (S)-(-)-(5-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propylamine hydrochloride 
• 1352917-67-9 (S)-1,2,3,4-tetrahydro-5-methoxy-N-propyl-naphthalen-2-ammonium (S)-2-hydroxy-3-phenylpropionate 
• 1352917-66-8 (S)-1,2,3,4-tetrahydro-5-methoxy-N-propyl-naphthalen-2-ammonium (R)-2-(2-chlorophenyl)-2-hydroxyacetate 
• 78598-91-1 2-(N-propylamino)-5-methoxytetraline 
• 5402-55-1 2-thiophenethanol 
• 3880-88-4 SKF 87967 hydrochloride 

Relevant articles and documents

Enantioselective Synthesis of β-Aminotetralins via Chiral Phosphoric Acid-catalyzed Reductive Amination of β-Tetralones

A new protocol for the synthesis of chiral β-aminotetralins has been developed via chiral phosphoric acid-catalyzed asymmetric reductive amination of β-tetralones using a Hantzsch ester as an organic hydride donor. Various chiral β-aminotetralins were obtained in good yields with good to high enantioselectivities. Furthermore, the utility of our new protocol was successfully demonstrated in the enantioselective synthesis of rotigotine. (Figure presented.).

IMPROVED PROCESS FOR THE PREPARATION OF CRYSTALLINE FORM II OF ROTIGOTINE

The present invention relates to an improved, environment friendly and cost effective process for the preparation of crystalline Form II of Rotigotine. Rotigotine, i.e. (6S)-6-{propyl[2-(2-thienyl) ethyl]amino}-5,6,7,8-tetrahydro-l-naphthalenol represented by structural formula (I), is used for the treatment of Parkinson's disease and Willis-Ekbom disease.

S-5-SUBSTITUENT-N-2'-(THIOPHENE-2-YL)ETHYL-TETRALIN-2-AMINE OR CHIRAL ACID SALTS THEREOF AND USE FOR PREPARING ROTIGOTINE

The chiral compound S-5-substituted-N-2-(thienyl-2-yl-)ethyl-tetralin-2-amine or its chiral acid salts and preparation method thereof are disclosed, and the method for preparing Rotigotine by using the chiral compound is also disclosed. Racemic 5-substituted-N-2'-(thien-2-yl-)ethyl-tetralin-2-amine (compound 1) is resolved by using a conventional chiral acid to obtain an optically pure chiral acid salt of S-5-substituted-N,2'-(thien-2-yl-)ethyl-tetralin-2-amine, which is then dissociated to obtain S-5-substituted-N-2'-(thien-2-yl-)ethyl-tetralin-2-amine (compound 2). The compound 2 or chiral acid salt thereof is alkylated and deprotected to produce rotigotine (compound 5).