101403-24-1

Basic information

• Product Name: (S)-1,2,3,4-tetrahydro-5-methoxy-N-propyl-2-Naphthalenamine(Rotigotine)
• Synonyms: (S)-1,2,3,4-tetrahydro-5-methoxy-N-propyl-2-Naphthalenamine(Rotigotine);(S)-1,2,3,4-Tetrahydro-5-methoxy-N-propyl-2-naphthalenamine;Rotigotine InterMediate;(S)-5-Methoxy-N-propyl-1,2,3,4-tetrahydronaphthalen-2-aMine;2-NaphthalenaMine, 1,2,3,4-tetrahydro-5-Methoxy-N-propyl-, (S)-
• CAS NO: 101403-24-1
• Molecular Formula: C₁₄H₂₁NO
• Molecular Weight: 219.32
• Product Categories: APIs Intermediate
• Mol File: 101403-24-1.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 346.117 °C at 760 mmHg
• Flash Point: 143.285 °C
• Appearance: /
• Density: 1.014 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.533
• PKA: 10.26±0.20(Predicted)
• CAS DataBase Reference: (S)-1,2,3,4-tetrahydro-5-methoxy-N-propyl-2-Naphthalenamine(Rotigotine)(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1,2,3,4-tetrahydro-5-methoxy-N-propyl-2-Naphthalenamine(Rotigotine)(101403-24-1)
• EPA Substance Registry System: (S)-1,2,3,4-tetrahydro-5-methoxy-N-propyl-2-Naphthalenamine(Rotigotine)(101403-24-1)

Safety Data

• Hazardous Substances Data: 101403-24-1(Hazardous Substances Data)

Usage

General Description

Rotigotine, also known by its brand name Neupro, is a chemical compound with the formula (S)-1,2,3,4-tetrahydro-5-methoxy-N-propyl-2-Naphthalenamine. It is a dopamine agonist that works by stimulating dopamine receptors in the brain, which helps to regulate motor control and mood. In medicine, it is used as a transdermal patch to treat Parkinson's disease and restless legs syndrome. It is also being investigated for its potential in treating other conditions such as depression and attention deficit hyperactivity disorder (ADHD). Rotigotine is available by prescription and should be used under the guidance of a healthcare professional. Common side effects include dizziness, nausea, and skin irritation at the application site.

InChI:InChI=1/C14H21NO/c1-3-9-15-12-7-8-13-11(10-12)5-4-6-14(13)16-2/h4-6,12,15H,3,7-10H2,1-2H3/t12-/m0/s1

Upstream product

• 244239-67-6 (S)-N-(5-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propionamide 
• 136247-07-9 2-(N-benzylamino)-5-methoxytetralin 
• 1222074-03-4 (S)-(-)-2-(N-propylamino)-5-methoxytetraline (+)-N-(3,5-dinitrobenzoyl)-α-phenylglycine salt 
• 107-10-8 propylamine 
• 32940-15-1 5-methoxy-2-tetralone 
• 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 
• 1374308-75-4 C₁₄H₁₉NO 
• 244239-68-7 (R)-N-(5-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propionamide 
• 58349-23-8 (S)-(-)-2-(N-benzylamino)-5-methoxytetralin 
• 58349-15-8 (S)-5-methoxy-1,2,3,4-tetrahydronaphthalen-2-amine hydrochloride 

Downstream Products

• 99755-59-6 rotigotine 
• 125572-93-2 rotigotine hydrochloride 
• 93601-86-6 (S)-(-)-(5-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propylamine hydrochloride 
• 1148154-91-9 (2S)-5-methoxy-N-propyl-N-(2'-(thien-2-yl)ethyl)tetralin-2-amine 
• 78598-91-1 2-(N-propylamino)-5-methoxytetraline 
• 1563175-00-7 (S)-5-methoxy-N-(2-(4-(3′-methoxybiphenyl-4-yl)piperazin-1-yl)ethyl)-N-propyl-1,2,3,4-tetrahydronaphthalen-2-amine 
• 165950-84-5 (S)-1,2,3,4-tetrahydro-5-hydroxy-N-propyl-naphthalen-2-ammonium hydrobromide 
• 136316-06-8 (S)-(-)-2--5-methoxytetralin 
• 129388-80-3 (S)-(-)-2--5-hydroxytetralin 
• 136247-11-5 N-((S)-5-Methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-2-(4-nitro-phenyl)-N-propyl-acetamide 
• 101470-23-9 Desthienyl-Rotigotine 

Relevant articles and documents

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.

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.

Preparation method for rotigotine

The invention discloses a preparation method for rotigotine. The preparation method includes the following steps: S1. performing an amination reduction reaction on a 5-methoxy-2-tetralone solution, tert-butanesulfinamide, a catalyst, and sodium borohydride to obtain a substance A; S2. performing an alkylation reaction on a solution of the substance A, bromopropane, and a basic catalyst to obtain asubstance B; S3. reacting the substance B with a hydrochloric acid methanol solution to obtain a substance C; S4. performing a reaction on the substance C, 2-(2-bromoethyl)thiophene, potassium carbonate, and N,N-dimethylformamide to obtain a substance D; and S5. reacting acetic acid with hydrogen bromide to obtain the rotigotine. The preparation method is simple in operation, is high in yield, ismild in reaction condition, is green and environmentally friendly, is high in purity of the prepared rotigotine, and is suitable for large-scale industrial production.

luo Ti gastrodia tuber of a kind of preparation method

The invention discloses a preparation method of rotigotine, and belongs to the technical field of medicine synthesis. According to the method, 5-methoxy-2-tetralone is used as a raw material for amination, asymmetric reduction, halogenation and methoxyl group removal four step reaction for synthesis of chiral rotigotine {(-)-(S)-2-(N-propyl-N-(2-(2-thiophene) ethyl] amino]-5-hydroxy-1, 2, 3, 4-tetralin}. According to the method, a simplex stereoscopic structural compound is synthesized by stereo selective chemical reaction, in the asymmetric reduction process, hantzsch ester 1, 4-dihydropyridine (HEH) is used as a reducing agent, and chiral phosphoric acid is used as a catalyst to synthesize an important intermediate (S)-2-(N-n-propyl) amido-5-methoxy tetralin (II) with a simplex stereoscopic structure, the use of a chiral reagent for splitting to obtain the simplex stereoscopic structural compound is avoided, the synthesis procedure is shortened, the yield is improveds, and the method is favorable for industrialized production.