13636-02-7

Usage

Uses

Used in Pharmaceutical Industry:
3-(Dimethylamino)-1-(2-thienyl)-1-propanol is used as a key intermediate in the synthesis of chitosan compounds, which are essential for the development of optical isomer separating agents. These agents play a crucial role in the purification and separation of optical isomers, which are vital in the production of various pharmaceuticals with specific therapeutic effects.
Used in Chemical Synthesis:
In the field of chemical synthesis, 3-(Dimethylamino)-1-(2-thienyl)-1-propanol serves as a valuable building block for the creation of more complex molecules with diverse applications. Its unique structure allows for further functionalization and modification, making it a versatile compound for researchers and chemists working on the development of new materials and products.
Used in Research and Development:
3-(Dimethylamino)-1-(2-thienyl)-1-propanol is also utilized in research and development settings, where it can be employed to study the properties and behavior of various chemical reactions and processes. Its unique structure and reactivity make it an interesting subject for scientific investigation, potentially leading to new discoveries and advancements in the field of chemistry.

InChI:InChI=1/C9H15NOS/c1-10(2)6-5-8(11)9-4-3-7-12-9/h3-4,7-8,11H,5-6H2,1-2H3

Upstream product

• 13196-35-5 3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one 
• 132335-49-0 α-[2-(dimethylamino)ethyl](thiophene-2-yl)methanol 
• 88-15-3 2-Acetylthiophene 
• 5424-47-5 3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride 
• 34772-98-0 3-dimethylamino-1-thiophen-2-ylpropenone 

Downstream Products

• 136436-86-7 Toluene-4-sulfonic acid 3-dimethylamino-1-thiophen-2-yl-propyl ester 
• 116817-11-9 N,N-dimethylamino-3-(1-naphthanyloxy)-3-(2-thienyl)-1-propanamine 
• 287737-72-8 (S)-N,N-dimethyl-N-[3-hydroxy-3-(2-thienyl)propyl]-ammonium (S)-mandelate 
• 132335-49-0 α-[2-(dimethylamino)ethyl](thiophene-2-yl)methanol 
• 116817-13-1 duloxetine 
• 116817-79-9 phenyl N-methyl-3-(1-naphthalenyloxy)-3-(2-thienyl)-propylcarbamate 
• 116817-12-0 N,N-dimethyl-3-(1-naphthalenyloxy)-3-(thien-2-yl)propanamine oxalate 
• 116817-12-0 N,N-dimethyl-3-(1-napthalenyloxy)-2-thiophenepropanamine oxalate 
• 132335-47-8 (S)-N,N-dimethyl-3-(1-naphthyloxy)-3-(2-thienyl)propanamine oxalate 
• 136434-34-9 duloxetine hydrochloride 
• 132335-46-7 N-methyl-(S)-duloxetine 
• 947686-09-1 (S)-N-methyl-N-phenoxycarbonyl-3-(1-naphthyloxy)-3-(2-thienyl)-1-propylamine 
• 1369583-87-8 N-[4-(2-methoxyphenylpiperazinyl)propionyl]-N-methyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine 
• 1369583-88-9 N-[4-(3-trifluoromethylphenylpiperazinyl)propionyl]-N-methyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine 

Relevant academic research and scientific papers

Preparation method of S-(+)duloxetine hydrochloride intermediate

The invention discloses a preparation method of a compound of a formula B (shown in the description). The preparation method comprises the steps of dissolving a compound of a formula A (shown in the description) in a solvent, and reacting under the effect of a reducing agent. Furthermore, the ee value of the compound of the formula B obtained by reducing in the presence of a complex, namely ferrocene, is over 98%. The preparation method provided by the invention is simple and feasible, the resolution or the chiral catalysis induction is not required, the product yield and the chiral purity arehigh, and the preparation method is suitable for the industrial production of S-(+)duloxetine hydrochloride intermediate.

Synthesis method of key intermediate for preparing duloxetine hydrochloride from 2-acetylthiophene

The invention provides a synthesis method of a key intermediate for preparing duloxetine hydrochloride from 2-acetylthiophene and belongs to the technical field of chemical synthesis. The synthesis method comprises the following steps: reacting cyanuric chloride and N,N-dimethylformamide with 2-acetylthiophene to obtain 3-(dimethylamino)-1-(2-thienyl)-2-propenyl-1-one; reducing 3-(dimethylamino)-1-(2-thienyl)-2-propenyl-1-one through lithium aluminum hydride to obtain a duloxetine hydrochloride intermediate which is (R,S)-N,N-dimethyl-3-hydroxy-3-(2-thienyl)propylamine. The synthesis method iscapable of synthesizing a target product which is a key intermediate of duloxetine hydrochloride through two-step reaction, is cheap in raw materials, simple in process, simple and convenient to operate, mild in reaction condition, short in reaction period and free of expensive catalysts, is environmentally friendly, and is suitable for industrial production; the prepared products are high in yield and purity.

New amine compound and use thereof in treatment of depression

The invention relates to a new amine compound and a use thereof in the treatment of depression, and concretely relates to a compound represented by formula I, optical isomers, solvates or pharmaceutically acceptable salts thereof, and a use thereof in the preparation of antidepressant drugs. Preclinical pharmacological studies show that the compound is comparable to and even better than first-line antidepressants (such as duloxetine).

Preparation of duloxetine hydrochloride

The invention belongs to the fields of organic chemistry and pharmaceutical chemistry, and particularly relates to a synthesis technique of duloxetine hydrochloride. By converting the R configuration compound into S configuration, compared with the duloxetine hydrochloride prepared from the single S-configuration compound, the total yield is enhanced by nearly 47%, and the production cost is lowered. 1-chloroethylchloroformate is used instead of phenyl chloro-formate to directly generate the duloxetine hydrochloride during demethylation, thereby reducing the salification step, shortening the production cycle and saving the cost.

A west Luo river sandbank chiral intermediate mandelic acid salt preparation method

A purpose of the present invention is to provide a method for simultaneously recycling (R)-(-)-N,N-dimethyl-3-(2-thienyl)-3-hydroxypropylamine (II) and S-mandelic acid to prepare a duloxetine chiral intermediate (S)-(-)-N,N-dimethyl-3-(2-thienyl)-3-hydroxypropylamine S-mandelate (I). The formulas (I) and (II) are defined in the instruction.

Preparation method of (S)-3-N,N-disubstituted amino-1-(2-thienyl)-1-propanol

The invention discloses a preparation method of (S)-3-N,N-disubstituted amino-1-(2-thienyl)-1-propanol shown as the formula (I). The method comprises: taking 2-acetyl thiophene shown in the formula (II) as a raw material, and allowing 2-acetyl thiophene to completely react with di(trichloromethyl)carbonic ester (III) and N,N-disubstituted methanamide (IV) in an organic solvent under the catalysis of an organic base to obtain N,N-disubstituted amino-1-(2-thienyl)-1-acrylketone shown as the formula (V); and performing hydrogenation reduction with lithium aluminium hydride to obtain N,N-disubstituted amino-1-(2-thienyl)-1-propanol shown as the formula (VI); and performing splitting with S-mandelic acid and recrystallization with ethyl acetate to obtain the target product shown as the formula (I). The preparation method is low in cost, mild in reaction condition, less in waste water, waste gas and industrial residue, small in energy consumption, and high in yield. The preparation method is safe and is suitable for industrial production.

Chemoenzymatic synthesis of (S)-duloxetine using carbonyl reductase from Rhodosporidium toruloides

A chemoenzymatic strategy was developed for (S)-duloxetine production employing carbonyl reductases from newly isolated Rhodosporidium toruloides into the enantiodetermining step. Amongst the ten most permissive enzymes identified, cloned, and overexpressed in Escherichia coli, RtSCR9 exhibited excellent activity and enantioselectivity. Using co-expressed E. coli harboring both RtSCR9 and glucose dehydrogenase, (S)-3-(dimethylamino)-1-(2-thienyl)-1-propanol 3a was fabricated with so far the highest substrate loading (1000 mM) in a space-time yield per gram of biomass (DCW) of 22.9 mmol L-1 h-1 g DCW-1 at a 200-g scale. The subsequent synthetic steps from RtSCR9-catalyzed (S)-3a were further performed, affording (S)-duloxetine with 60.2% overall yield from 2-acethylthiophene in >98.5% ee.

METHOD FOR PRODUCING DULOXETINE HYDROCHLORIDE

PROBLEM TO BE SOLVED: To provide a new method for producing (S)-(+)-N-methyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine hydrochloride (general name: duloxetine hydrochloride) useful as an antidepressant. SOLUTION: In a method for producing duloxetine hydrochloride, a solution obtained by dissolving a crude product containing duloxetine hydrochloride in a dissolving solvent (a first dissolution step) and acetone are mixed (a mixing step), the duloxetine hydrochloride precipitated in the obtained mixed solution is temporarily dissolved (a second dissolution step), and then the duloxetine hydrochloride is precipitated. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT

OLIGOMER-ARYLOXY-SUBSTITUTED PROPANAMINE CONJUGATES

The invention relates to (among other things) oligomer- aryloxy-substituted propanamine conjugates and related compounds. A conjugate of the invention, when administered by any of a number of administration routes, exhibits advantages over un-conjugated aryloxy-substituted propanamine compounds.

ARALKYL DIAMINE DERIVATIVES AND USES THEREOF AS ANTIDEPRESSANT

Aralkyl diamine derivative of the following formula, pharmaceutically acceptable salts or uses thereof as antidepressants. The derivatives have triplex inhibiting activities of the reuptake of 5-HT, dopamine and noradrenalin, which can be administered to the patients in need of such treatment in the form of compositions orally or injectedly et al.