244239-67-6

Basic information

• Product Name: N-[(2S)-5-methoxytetralin-2-yl]propanamide
• Synonyms: Rotigotine Impurity 26;Rotigotine Impurity 20;(S)-5-methoxy-2-propionamidotetralin;(S)-N-(5-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propionamide;N-[(2S)-1,2,3,4-Tetrahydro-5-methoxy-2-naphthalenyl]propanamide;Propanamide, N-[(2S)-1,2,3,4-tetrahydro-5-methoxy-2-naphthalenyl]-
• CAS NO: 244239-67-6
• Molecular Formula: C₁₄H₁₉NO₂
• Molecular Weight: 233.31
• Mol File: 244239-67-6.mol

Chemical Properties

• Boiling Point: 447.8°C at 760 mmHg
• Flash Point: 224.6°C
• Density: 1.09g/cm³
• Vapor Pressure: 3.27E-08mmHg at 25°C
• Refractive Index: 1.542
• CAS DataBase Reference: N-[(2S)-5-methoxytetralin-2-yl]propanamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[(2S)-5-methoxytetralin-2-yl]propanamide(244239-67-6)
• EPA Substance Registry System: N-[(2S)-5-methoxytetralin-2-yl]propanamide(244239-67-6)

Safety Data

• Hazardous Substances Data: 244239-67-6(Hazardous Substances Data)

Upstream product

• 79-03-8 propionyl chloride 
• 58349-15-8 (S)-5-methoxy-1,2,3,4-tetrahydronaphthalen-2-amine hydrochloride 
• 105086-92-8 (S)-5-methoxy-2-amino-1,2,3,4-tetrahydronaphthalene 
• 4018-91-1 2-Amino-5-methoxy-1,2,3,4-tetrahydronaphthalene 
• 1321942-91-9 N-(5-methoxy-3,4-dihydronaphthalen-2-yl)propionamide 
• 32940-15-1 5-methoxy-2-tetralone 

Downstream Products

• 1148154-91-9 (2S)-5-methoxy-N-propyl-N-(2'-(thien-2-yl)ethyl)tetralin-2-amine 
• 99755-59-6 rotigotine 
• 101403-24-1 (S)-(5-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propylamine hydrochloride 

Relevant articles and documents

Preparation method of rotigotine

The invention relates to the technical field of medicine preparation, and discloses a preparation method of rotigotine, which comprises the following steps: by taking 5-methoxy-2-tetralone as an initial raw material, reacting with R-alpha-methylbenzylamine, performing debenzylation reduction and S-mandelic acid chiral resolution, then reacting with a propionyl chloride reagent to generate an amide compound, and then reducing by a sodium borohydride reagent to obtain the rotigotine; and finally, reacting with 2-(thiophene-2-yl) 2-nitric acid benzene sulfonic acid ethyl ester to obtain the rotigotine. The preparation process route is as follows: the rotigotine is mild in preparation condition, simple and convenient to operate, relatively high in yield of key intermediates, high in optical purity and easy for industrial large-scale production, and has a very good application prospect.

New catalytic route for the synthesis of an optically active tetralone-derived amine for rotigotine

Rotigotine is a launched drug for the treatment of Parkinson's disease and restless legs syndrome. The key steps of an alternative route for the synthesis of rotigotine have been demonstrated. Formation of a prochiral enamide, asymmetric hydrogenation of the enamide with high enantioselectivity, and reduction of the resulting amide to an amine have been proved to work successfully. The best conditions screened to date for the asymmetric hydrogenation of enamide 9 to amide 10 were with [(RuCl((R)-T-BINAP))2(μ-Cl)3][NH2Me2] at 25 bar H2 and 30 °C (500:1 S/C ratio, 99% conversion, 91% ee S). Reduction of amide 10 to amine 5 was best achieved with Red-Al giving 95% conversion.

Novel Process for the Preparation of Nitrogen Substituted Aminotetralins Derivatives

The present invention provides an alternative synthesis of N-substituted aminotetralines which synthesis comprises catalytic asymmetric hydrogenation of compounds of general formula (A).

Synthesis and pharmacology of the enantiomers of the potential atypical antipsychotic agents 5-OMe-BPAT and 5-OMe-(2,6-di-OMe)-BPAT

The optically pure enantiomers of the potential atypical antipsychotic agents 5-methoxy-2-[N-(2-benzamidoethyl)-N-n-propylamino]tetralin (5-OMe-BPAT, 5) and 5-methoxy-2-{N-[2-(2,6-dimethoxy)benzamidoethyl]-N-n-propylamino}tetralin [5-OMe-(2,6-di-OMe)-BPAT