185517-74-2

Usage

Uses

Used in Pharmaceutical Industry:
(S)-2,3-DIHYDRO-N-METHYL-N-2-PROPYNYL-1H-INDEN-1-AMINE is used as a key intermediate in the synthesis of various therapeutic agents and drugs. Its unique structure and properties contribute to the development of innovative medications.
Used as a Selective Serotonin Reuptake Inhibitor (SSRI):
In the field of mental health, (S)-2,3-DIHYDRO-N-METHYL-N-2-PROPYNYL-1H-INDEN-1-AMINE is used as a selective serotonin reuptake inhibitor (SSRI) for its potential role in the treatment of depression and other mood disorders. Its pharmacological action helps regulate serotonin levels in the brain, providing relief from depressive symptoms.
Used in Research and Development:
(S)-2,3-DIHYDRO-N-METHYL-N-2-PROPYNYL-1H-INDEN-1-AMINE is also utilized in research and development for exploring its potential applications in treating various mental health disorders. Its unique properties make it a promising candidate for further studies and the development of novel therapeutic agents.

InChI:InChI=1/C12H13N/c1-2-9-13-12-8-7-10-5-3-4-6-11(10)12/h1,3-6,12-13H,7-9H2/t12-/m0/s1

Upstream product

• 6165-75-9 propargyl benzenesulfonate 
• 34698-41-4 2,3-dihydro-1H-inden-1-amine 
• 83-33-0 inden-1-one 
• 2450-71-7 Propargylamine 
• 1506-18-9 S-(-)-N-propargyl-1-aminoindan hydrochloride 
• 15430-52-1 prop-2-yn-1-amine hydrochloride 
• 1227784-59-9 N-(2,3-dihydroinden-1-ylidene)prop-2-yn-1-amine 
• 1227784-60-2 N-(2-propynyl)-indanyl-imine hydrochloride 
• 624-65-7 2-propynyl chloride 
• 68253-35-0 indan-1-one oxime 
• 915797-28-3 (R)-N-indan-1-yl-4-nitro-N-prop-2-ynyl-benzenesulfonamide 
• 496-11-7 INDANE 
• 217640-41-0 (R)-N-indan-1-yl-4-nitrobenzenesulfonamide 
• 10277-74-4 (R)-1-Aminoindane 

Downstream Products

• 136236-51-6 rasagiline 
• 1179031-47-0 N-(2-chloroallyl)-2,3-dihydro-1H-inden-1-amine 
• 1175018-74-2 N-2-propene-1-yl-3-chloro-cis-(R)-aminoindan 
• 1175018-79-7 N-2-propene-1-yl-3-chloro-trans-(R)-aminoindan 
• 1175018-73-1 (R)-N-(2-chloroallyl)-2,3-dihydro-1H-inden-1-amine 
• 124192-86-5 N-Methyl Rasagiline 
• 1875-50-9 N-propargyl-1-aminoindan 

Relevant academic research and scientific papers

Trimethyl Borate-Catalyzed, Solvent-Free Reductive Amination

Solvent-free reductive amination of aldehydes and ketones with aliphatic and aromatic amines in high-to-excellent yields has been achieved with sub-stoichiometric trimethyl borate as promoter and ammonia borane as reductant.

Enantioselective synthesis of 1-aminoindene derivativesviaasymmetric Br?nsted acid catalysis

We describe a catalytic asymmetric iminium ion cyclization reaction of simple 2-alkenylbenzaldimines using a BINOL-derived chiralN-triflyl phosphoramide. The corresponding 1-aminoindenes and tetracyclic 1-aminoindanes are formed in good yields and high enantioselectivities. Further, the chemical utility of the obtained enantiopure 1-aminoindene is demonstrated for the asymmetric synthesis of (S)-rasagiline.

Improved preparation method of rasagiline racemic intermediate

The invention discloses an improved preparation method of a rasagiline racemic intermediate, belongs to the technical field of medicinal chemistry, and particularly relates to an improved method for preparing an N-(2-propargyl)-2,3-dihydro-1H-indene-1-amine racemic body. According to the invention, the N-(2-propargyl)-2,3-dihydro-1H-indene-1-amine racemic body is prepared by using 1-indanone and propargylamine as raw materials through a one-pot method in the presence of a dehydrating agent; and the method is simple to operate, high in yield and good in purity, and establishes a good foundationfor subsequent preparation of rasagiline mesylate.

Improved method for preparing rasagiline

The invention provides an improved method for preparing rasagiline, which comprises the following steps: by using a micro-channel reactor, reacting R-(-)-1-aminoindane (structural formula II) servingas a raw material with a propargyl derivative (structural formula III) in the presence of a proper solvent, temperature, alkali and the like to obtain R-(+)-N-propargyl-1-aminoindane (structural formula I), and salifying to obtain rasagiline mesylate. The reaction formula is shown in the specification. According to the method, a dialkyl substitution by-product N,N-dipropargyl-1-aminoindane can bereduced, the rasagiline and the salt thereof can be prepared with a high yield and high purity, the reaction time is shortened, the reaction conditions can resist high temperature and high pressure, the post-treatment is simple, the dialkyl substitution by-product is easy to remove, the unreacted R-(-)-1-aminoindane can be separated and recycled, and the cost is low, and the method is suitable forindustrial production.

Protic additives or impurities promote imine reduction with pinacolborane

We report here that addition of stoichiometric amounts of alcohols or water to mixtures of imines and pinacolborane promote reduction reactions. The reactions of several imines were examined, revealing that alkyl imines were reduced, while aniline derived imines were not effectively reduced. The use of binol as an additive resulted in modest enantioinduction, however other chiral additives that were screened gave negligible enantioinduction. While the reactions described herein are not competitive in conversion with established imine reduction technologies, this work reveals that the presence of protic impurities must be considered as a promoter of side reactions in catalyzed imine hydroborations. Amines also promote imine reduction in certain cases, raising the possibility of a slow autocatalytic reaction. The ability of water or other protic impurities to promote the reduction of imines with pinacolborane represents an important identification of a potential source of background reaction in catalyzed reductions of imines.

CHIRAL CATALYST AND METHOD FOR ASYMMETRIC REDUCTION OF AN IMINE

The present disclosure discusses (i) a compound having a chemical formula according to Formula (I), or its enantiomer; and (ii) a compound that is reactive with a hydride to produce a compound having a chemical formula according to Formula (I), or its enantiomer. Formula (I) is: Formula (I) where R1 and R2 are H, optionally substituted C1-C3 alkyl, or linked together to form an optionally substituted C3 or C4 alkyl group; R3 and R3' are H; R4 and R4' are the same, and are optionally substituted C1-C6 alkyl; and R5 and R5' are the same, and are optionally substituted aryl or heteroaryl. In some examples, R4 and R5 are linked, and R4' and R5' are linked, where both linking groups are the same. The present disclosure also discusses methods of asymmetric reduction of an imine, and methods of forming the catalysts and pre-catalysts.

Preparation method of rasagiline mesylate and intermediate thereof

The invention discloses a preparation method of rasagiline mesylate and an intermediate thereof. The invention provides the preparation method of rasagiline mesylate I. The preparation method comprises the following steps: S1, in an organic solvent, in the presence of a reducer and a catalyst, carrying out a reduction reaction on a rasagiline mesylate intermediate II and the reducer to obtain a rasagiline mesylate intermediate III; and S2, in an organic solvent, carrying out a salt forming reaction on the rasagiline mesylate intermediate III obtained in the S1 and methanesulfonic acid to obtain rasagiline mesylate I. The preparation method does not employ an amino alkylation reaction which is relatively more in side reaction, and the prepared rasagiline mesylate I is high in purity, reaches the demand on bulk pharmaceutical chemicals, the purity is greater than 99.5%, the maximum single impurities are smaller than 0.10%, the yield is high, the production cost is low, and the method issuitable for industrial production. The formula is as shown in the description.

Intermolecular Radical C(sp3)?H Amination under Iodine Catalysis

The direct amination of aliphatic C?H bonds has remained one of the most tantalizing transformations in organic chemistry. Herein, we report on a unique catalyst system, which enables the elusive intermolecular C(sp3)?H amination. This practical synthetic strategy provides access to aminated building blocks and fosters innovative multiple C?H amination within a new approach to aminated heterocycles. The synthetic utility is demonstrated by the synthesis of four relevant pharmaceuticals.

Kinetic Resolution and Deracemization of Racemic Amines Using a Reductive Aminase

The NADP(H)-dependent reductive aminase from Aspergillus oryzae (AspRedAm) was combined with an NADPH oxidase (NOX) to develop a redox system that recycles the co-factor. The AspRedAm-NOX system was applied initially for the kinetic resolution of a variety of racemic secondary and primary amines to yield S-configured amines with enantiomeric excess (ee) values up to 99 %. The addition of ammonia borane to this system enabled the efficient deracemization of racemic amines, including the pharmaceutical drug rasagiline and the natural product salsolidine, with conversions up to >98 % and >99 % ee Furthermore, by using the AspRedAm W210A variant it was possible to generate the opposite R enantiomers with efficiency comparable to, or even better than, the wildtype AspRedAm.

Diazaphospholene Precatalysts for Imine and Conjugate Reductions

The first examples of 1,3,2-diazaphospholene-catalyzed imine reduction and conjugate reduction reactions are reported. This approach employs readily synthesized alkoxydiazaphospholene precatalysts that can be handled in open air. Reduction of substrates containing Lewis basic functionality, isolated unsaturation, and protic functional groups was accomplished. The synthetic utility of this approach is demonstrated by the synthesis of the important antiparkinson medicine rasagiline and the natural product zingerone.