60612-23-9

Usage

Uses

Used in Pharmaceutical Industry:
N-(2-Chlorobenzyl)-2-(2-thienyl)ethylamine hydrochloride is used as a key intermediate in the preparation of acid addition salts of 4,5,6,7-tetrahydrothieno(3,2-c)pyridine derivatives. These derivatives possess significant antithrombotic activity, making them valuable in the development of medications aimed at preventing blood clot formation and related thrombotic disorders.
N-(2-CHLOROBENZYL)-2-(2-THIENYL)ETHYLAMINE HYDROCHLORIDE's role in the synthesis of antithrombotic agents underscores its importance in the pharmaceutical sector, where it contributes to the creation of life-saving drugs that can help manage and treat cardiovascular conditions. Its application in this context highlights the significance of organic chemistry in advancing modern medicine and improving patient outcomes.

InChI:InChI=1/C13H14ClNS.ClH/c14-13-6-2-1-4-11(13)10-15-8-7-12-5-3-9-16-12;/h1-6,9,15H,7-8,10H2;1H

Upstream product

• 40412-06-4 2-(2-thienyl)ethyl tosylate 
• 89-97-4 2-CHLOROBENZYLAMINE 
• 5402-55-1 2-thiophenethanol 
• 75-21-8 oxirane 
• 98-59-9 p-toluenesulfonyl chloride 
• 2786-07-4 2-thienyl lithium 
• 143810-09-7 N-(2-chlorobenzyl)-2,2-dioxo-1,2,3-oxathiazolidine 

Downstream Products

• 53885-35-1 ticlopidine hydrochloride 

Relevant academic research and scientific papers

Novel preparation method for ticlopidine hydrochloride

The invention provides a novel preparation method for ticlopidine hydrochloride. The method comprises the following steps: with thiopheneethanol as a raw material, reacting thiopheneethanol with p-toluene sulfonyl chloride under the action of an acid binding agent so as to protect and activate a hydroxyl group; then subjecting a reaction product obtained in the previous step and o-chlorobenzylamine to a condensation reaction; and carrying out a ring closure reaction on a condensation reaction product and 1,3-dioxolane so as to obtain ticlopidine hydrochloride. The novel preparation method has the advantages of mild reaction conditions, low production cost, high product yield, good product quality and easy realization of industrial production.

Method for synthesizing ticlopidine hydrochloride

The invention provides a method for synthesizing ticlopidine hydrochloride. The method comprises the following steps of taking thiopheneethanol as a raw material, and protecting and activating hydroxyl by means of reacting the thiopheneethanol with paratoluensulfonyl chloride under the action of an acid-binding agent; then performing a condensation reaction with o-chlorobenzylamine; performing a ring closing reaction with 1,3-dioxolane under an acidic condition so as to obtain the ticlopidine hydrochloride. The method provided by the invention has the advantages of mild reaction condition, low production cost, high product yield, good quality and convenience for industrialized production.

Method for preparing ticlopidine hydrochloride

The invention provides a method for preparing ticlopidine hydrochloride, which comprises the following steps: reacting thienyl ethanol used as a raw material with paratoluensulfonyl chloride under the action of an acid-binding agent to protect and activate the hydroxy group; carrying out condensation reaction with ortho-chlorobenzylamine; and carrying out cyclization reaction with 1,3-dioxolane under acidic conditions to obtain the ticlopidine hydrochloride. The method has the advantages of mild reaction conditions, low production cost, high product yield and good product quality, and is convenient for industrial production.

Preparation method of ticlopidine hydrochloride

The invention provides a preparation method of ticlopidine hydrochloride. The preparation method comprises the following steps: reacting thiophene ethanol as a raw material with paratoluensulfonyl chloride at first under the action of an acid-binding agent so as to protect and activate hydroxyl radicals; then performing condensation reaction with o-chlorobenzylamine; and then under an acidic condition, performing ring-closing reaction with 1,3-dioxolane to obtain ticlopidine hydrochloride. The preparation method is mild in reaction condition, low in production cost, high in product yield and good in product quality, and can conveniently realize industrial production.

N-2-chlorobenzyl-2-oxo and N-2-chlorobenzyl-2,2-dioxo-1,2,3-oxathiazolidine derivatives, their preparation and synthesis of thieno[3,2-c]pyridine derivatives therefrom

Compounds of the formula: STR1 wherein: A is oxo or dioxo; R1, R2 and R3 are independently hydrogen or lower alkyl of one to six carbon atoms; R4, R5, R6 and R7 are independently hydrogen, lower alkyl of one to six carbon atoms, alkoxy, acyl or halo; are advantageously converted to thieno[3,2-c]pyridine derivatives and the pharmaceutically acceptable salts thereof, particularly ticlopidine hydrochloride.

Process for the preparation of 2-(thien-2-yl)- and 2-(thien-3-yl)-ethylamine derivatives

The present invention provides a multistep process for the preparation of 2-(thien-2-yl)- and 2-(thien-3-yl)-ethylamine intermediates of the general formula:- STR1 in which R1, in the 2-, 3-, 4- or 5-position, is a hydrogen or halogen atom, a nitro, amino, cyano or carboxyl group, a linear or branched alkyl or alkoxy radical or a heterocyclic or non-heterocyclic aromatic radical, which is optionally mono- or polysubstituted, R2 is a hydrogen atom, a linear or branched alkyl radical or a heterocyclic or non-heterocyclic aromatic radical, which is optionally mono- or polysubstituted, and Ar is a heterocyclic or non-heterocyclic aromatic radical, which is optionally mono- or polysubstituted, when the aminoethyl radical is in the two position and the radical R1 is in the 4- or 5-position, the above intermediates can be converted into 4,5,6,7-tetrahydrothieno[3,2-c]pyridine derivatives according to a procedure set forth in U.S. Pat. No. 4,127,580. When the aminoethyl radical is in the 3-position and the radical R1 is in the 4- or 5-position, the above intermediates can be converted into 4,5,6,7-tetrahydrothieno[2,3-c]pyridine derivatives according to a procedure set forth in U.S. Pat. No. 4,127,580. Both sets of tetrahydrothieno pyridine final products possess anti-inflammatory, vasodilator and blood platelet aggregation inhibition activity.

Process for the preparation of 2-(thienyl-2)-and 2-(thienyl-3)-ethylamines

The present invention provides a process for the preparation of 2-(thienyl-2)- and 2-(thienyl-3)-ethylamines of the general formula: STR1 in which R1, which is in the 2-, 3-, 4- or 5-position, is a hydrogen atom, a straight-chained or branched alkyl radical or a heterocyclic or non-heterocyclic aromatic radical, which is optionally mono- or polysubstituted, or R1 is an alkoxy radical, a halogen atom or a nitro, carboxyl, cyano or amino group; the aminoethyl chain is in the 2- or 3-position of the thiophene nucleus; R2 is a hydrogen atom or a straight-chained or branched alkyl radical or a heterocyclic or non-heterocyclic aromatic radical, which is optionally mono- or poly-substituted; and Ar is a heterocyclic or non-heterocyclic aromatic radical, which is optionally mono- or poly-substituted.

Process for the preparation of 2-(thien-2-yl)- and 2-(thien-3-yl)-ethylamine derivatives

The present invention provides a process for the preparation of 2-(thien-2-yl)- and 2-(thien-3-yl)-ethylamine derivatives of the general formula: STR1 in which R1, in the 2-, 3-, 4- or 5-position, is a hydrogen or halogen atom, a nitro, carboxyl, cyano or amino group, a linear or branched alkyl or alkoxy radical or a heterocyclic or non-heterocyclic aromatic radical, which is optionally mono- or polysubstituted, the aminoethyl chain is in the 2- or 3-position, R2, R3 and R4, which are the same or different, are hydrogen atoms or heterocyclic or non-heterocyclic aromatic radicals, which are optionally mono- or polysubstituted, and Ar is a heterocyclic or non-heterocyclic aromatic radical, which is optionally mono- or polysubstituted.

Process for the preparation of thieno-pyridine derivatives

This invention relates to a process for the preparation of thieno-pyridine derivatives having the structural formula: STR1 in which R1 represents an optionally substituted alkyl, aryl or aralkyl radical, and R2 and R3 represnt each hydrogen or a lower alkyl, aryl or heterocyclic radical, comprising: (a) reacting a derivative of the formula STR2 in which R2 and R3 are as defined for formula (I) and X represents hydrogen, or an alkali metal, or a radical Mg-Y in which Y represents halogen, with a halo-sulfonyl derivative having the formula: in which Hal represents halogen and R4 represents an optionally substituted alkyl, aryl or aralkyl group, to give a compound having the formula: STR3 (b) subsequently reacting the latter compound with an amine of the formula: in which R1 is as defined for the formula (I), to give a compound having the formula: STR4 and (c) subsequently cyclizing compound (VI) with formaldehyde to give the derivative of the formula (I).