1148154-91-9

Basic information

• Product Name: (S)-5-Methoxy-N-propyl-N-(2-(thiophen-2-yl)ethyl)-1,2,3,4-tetrahydronaphthalen-2-aMine
• Synonyms: (S)-5-methoxy-N-propyl-N-(2'-(thien-2-yl-)ethyl)-tetralin-2-amine;(S)-5-Methoxy-N-propyl-N-(2-(thiophen-2-yl)ethyl)-1,2,3,4-tetrahydronaphthalen-2-aMine;(2S)-5-methoxy-N-propyl-N-(2-thiophen-2-ylethyl)-1,2,3,4-tetrahydronaphthalen-2-amine
• CAS NO: 1148154-91-9
• Molecular Formula: C₂₀H₂₇NOS
• Molecular Weight: 329.49948
• Mol File: 1148154-91-9.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 473.5±45.0 °C(Predicted)
• Appearance: /
• Density: 1.10±0.1 g/cm3(Predicted)
• PKA: 8.92±0.20(Predicted)
• CAS DataBase Reference: (S)-5-Methoxy-N-propyl-N-(2-(thiophen-2-yl)ethyl)-1,2,3,4-tetrahydronaphthalen-2-aMine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-5-Methoxy-N-propyl-N-(2-(thiophen-2-yl)ethyl)-1,2,3,4-tetrahydronaphthalen-2-aMine(1148154-91-9)
• EPA Substance Registry System: (S)-5-Methoxy-N-propyl-N-(2-(thiophen-2-yl)ethyl)-1,2,3,4-tetrahydronaphthalen-2-aMine(1148154-91-9)

Safety Data

• Hazardous Substances Data: 1148154-91-9(Hazardous Substances Data)

Usage

Description

(S)-5-Methoxy-N-propyl-N-(2-(thiophen-2-yl)ethyl)-1,2,3,4-tetrahydronaphthalen-2-aMine is a complex organic compound characterized by its unique molecular structure. It is a chiral molecule with an (S) configuration, which means it has a specific three-dimensional arrangement of atoms. (S)-5-Methoxy-N-propyl-N-(2-(thiophen-2-yl)ethyl)-1,2,3,4-tetrahydronaphthalen-2-aMine is derived from the tetrahydronaphthalene class of compounds and features a methoxy group, a propyl chain, and a thiophen-2-ylethyl moiety attached to its structure. Its synthesis and properties make it a potential candidate for various applications in the pharmaceutical and chemical industries.

Uses

Used in Pharmaceutical Industry:
(S)-5-Methoxy-N-propyl-N-(2-(thiophen-2-yl)ethyl)-1,2,3,4-tetrahydronaphthalen-2-aMine is used as an active pharmaceutical ingredient (API) for the development of novel drugs targeting specific receptors or enzymes in the human body. Its unique structure allows for potential interactions with biological targets, making it a promising candidate for the treatment of various diseases and disorders.
Used in Chemical Research:
In the field of chemical research, (S)-5-Methoxy-N-propyl-N-(2-(thiophen-2-yl)ethyl)-1,2,3,4-tetrahydronaphthalen-2-aMine can be used as a starting material or intermediate in the synthesis of more complex molecules. Its unique structural features can be exploited to create new compounds with potential applications in various industries, such as materials science, agrochemicals, and environmental science.
Used in Drug Synthesis as an Impurity:
(S)-5-Methoxy-N-propyl-N-(2-(thiophen-2-yl)ethyl)-1,2,3,4-tetrahydronaphthalen-2-aMine may also be used as an impurity in the synthesis of other drugs. For example, it could be an impurity in the production of Rotigotine (R700700), a non-ergot dopamine agonist drug used for the treatment of Parkinson's disease. The presence of this compound as an impurity may affect the drug's efficacy, safety, or stability, and thus, its control and monitoring are essential during the drug manufacturing process.

Upstream product

• 1232344-40-9 (-)-(S)-5-methoxy-2-[N-2-(2-thienyl)ethylamino]tetraline 
• 802294-64-0 propionic acid 
• 244239-67-6 (S)-N-(5-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propionamide 
• 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 
• 1222074-06-7 2-(thiophen-2-yl)ethyl 2-nitrobenzene-1-sulfonate 
• 101403-24-1 (S)-(5-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propylamine hydrochloride 
• 32940-15-1 5-methoxy-2-tetralone 
• 1374308-75-4 C₁₄H₁₉NO 
• 26478-16-0 2-(2-Bromoethyl)thiophene 
• 19995-38-1 2-(thien-2-yl)ethyl chloride 
• 107-08-4 1-iodo-propane 

Downstream Products

• 125572-93-2 rotigotine hydrochloride 
• 1232344-37-4 (2S)-5-methoxy-N-propyl-N-(2'-(thien-2-yl)ethyl)tetralin-2-amine hydrochloride 
• 99755-59-6 rotigotine 

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.

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.

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).