93601-86-6

Basic information

• Product Name: (S)-1,2,3,4-Tetrahydro-5-methoxy-N-propyl-2-naphthalenamine hydrochloride
• Synonyms: (S)-1,2,3,4-Tetrahydro-5-methoxy-N-propyl-2-naphthalenamine hydrochloride;4-Tetrahydro-5-Methoxy-N-propyl-2-naphthalenaMine hydrochloride;(S)-5-Methoxy-N-propyl-1,2,3,4-tetrahydronaphthalen-2-aMine hydrochloride;(S)-(-)-(5-Methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propylaMine hydrochloride;(S)-5-Methoxy-N-propyl-2-AMinotetralin Hydrochloride;2-NaphthalenaMine, 1,2,3,4-tetrahydro-5-Methoxy-N-propyl-, hydrochloride, (S)-;(S)-2-NaphthalenaMine,1,2,3,4-tetrahydro-5-Methoxy-N-propyl-, hydrochloride;(S)-5-methoxy-N-propyl-2-aminotetraline hydrochloride
• CAS NO: 93601-86-6
• Molecular Formula: C₁₄H₂₁NO*ClH
• Molecular Weight: 255.787
• Product Categories: Amines;Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 93601-86-6.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• Density: 1.19g/cm3 at 20℃
• Vapor Pressure: 0-0Pa at 20-25℃
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), DMSO, Methanol (Slightly)
• Stability: Unstable in Aqueous Solution
• CAS DataBase Reference: (S)-1,2,3,4-Tetrahydro-5-methoxy-N-propyl-2-naphthalenamine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1,2,3,4-Tetrahydro-5-methoxy-N-propyl-2-naphthalenamine hydrochloride(93601-86-6)
• EPA Substance Registry System: (S)-1,2,3,4-Tetrahydro-5-methoxy-N-propyl-2-naphthalenamine hydrochloride(93601-86-6)

Safety Data

• Hazardous Substances Data: 93601-86-6(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Upstream product

• 1256261-00-3 (3aS,9bR)-6-methoxy-3-propyl-3,3a,4,5-tetrahydronaphtho[2,1-d]oxazol-2(9bH)-one 
• 3880-88-4 SKF 87967 hydrochloride 
• 78598-91-1 2-(N-propylamino)-5-methoxytetraline 
• 1352917-66-8 (S)-1,2,3,4-tetrahydro-5-methoxy-N-propyl-naphthalen-2-ammonium (R)-2-(2-chlorophenyl)-2-hydroxyacetate 
• 1352917-67-9 (S)-1,2,3,4-tetrahydro-5-methoxy-N-propyl-naphthalen-2-ammonium (S)-2-hydroxy-3-phenylpropionate 
• 1352917-68-0 (S)-1,2,3,4-tetrahydro-5-methoxy-N-propyl-naphthalen-2-ammonium (S)-2-methoxy-2-phenylacetate 
• 101403-25-2 (R)-1,2,3,4-tetrahydro-5-methoxy-N-propyl-naphthalen-2-amine 
• 3904-24-3 (5-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propylamine hydrochloride 
• 101403-24-1 (S)-(5-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propylamine hydrochloride 
• 32940-15-1 5-methoxy-2-tetralone 

Downstream Products

• 165950-84-5 (S)-1,2,3,4-tetrahydro-5-hydroxy-N-propyl-naphthalen-2-ammonium hydrobromide 
• 68643-08-3 (2S)-5-hydroxy-2-(di-n-propylamino)tetralin 
• 99755-59-6 rotigotine 
• 125572-93-2 rotigotine hydrochloride 

Relevant articles and documents

Preparation method of (S)-1, 2, 3, 4-tetrahydro-5-methoxy-N-propyl-2-naphthylamine hydrochloride

The invention relates to a preparation method of (S)-1, 2, 3, 4-tetrahydro-5-methoxy-N-propyl-2-naphthylamine hydrochloride, which is characterized by comprising the following steps: step 1, in the presence of a reducing agent, carrying out reductive amination reaction on (S)-1, 2, 3, 4-tetrahydro-5-methoxy-N-((R)-1-benzyl)-2-naphthylamine and propionaldehyde under acidic conditions to obtain a compound II; and step 2, carrying out a catalytic hydrogenation reaction on the compound II in the presence of a hydrogenation catalyst, and carrying out salifying in the presence of a salifying agent to obtain (S)-1, 2, 3, 4-tetrahydro-5-methoxy-N-propyl-2-naphthylamine hydrochloride. The invention also relates to the compound II.

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 comprising resolution of N-substituted aminotetralins of formula (II), wherein R1, R2 and R3 are as defined for compound of formula (I).