- Preparation method of ticlopidine hydrochloride
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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.
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Paragraph 0020; 0021
(2017/03/25)
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- Method for preparing ticlopidine hydrochloride
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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.
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Paragraph 0015; 0019
(2016/12/16)
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- Novel preparation method for ticlopidine hydrochloride
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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.
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Paragraph 0019
(2016/10/17)
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- A method for preparing pyridine [...] of hydrochloric acid
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The invention discloses a preparation method of ticlopidine hydrochloride. The preparation method comprises the following steps: A, adding a certain amount of reactive raw materials into a reaction container, and carrying out reaction at the temperature of 30-80 DEG C for 1-10 hours, wherein the raw materials include 2-thiophene ethylamine, methanal, a haloalkane solvent and a solid super acidic catalyst; B, cooling the solution of reaction to room temperature; C, adding a certain amount of a solid alkaline catalyst and 2-chlorobenzyl chloride into the solution of reaction, carrying out reaction at the temperature of 30-80 DEG C for 1-10 hours, stopping heating, and standing to precipitate; D, filtering to obtain a filtrate; and E, introducing hydrogen chloride into the filtrate to obtain ticlopidine hydrochloride. The solid super acidic catalyst and the solid alkaline catalyst are adopted by the preparation method, and the heterogeneous tandem reaction is carried out. The technology has the advantage of convenience in post-treatment, is easy to operate, can not cause corrosion to equipment and is economical, practical and environment-friendly, less three wastes are produced, and the solid acid and alkali can be reused.
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Paragraph 0060-0062
(2018/02/04)
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- Method for synthesizing ticlopidine hydrochloride
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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.
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Paragraph 0020; 0021
(2016/10/31)
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- Method for synthesizing ticlopidine hydrochloride
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The invention provides a method for synthesizing ticlopidine hydrochloride. The method comprises the following steps: by using thiopheneethanol as a raw material, under the action of an acid binding agent, firstly, performing a reaction on the thiopheneethanol and paratoluensulfonyl chloride to carry out protection and activation on hydroxy; performing a condensation reaction with chlorobenzylamine; then under an acid condition, performing a ring closing reaction with 1,3-dioxolane to obtain the ticlopidine hydrochloride. The method is mild in reaction condition, low in production cost, high in product yield and high in quality, and is convenient for industrial production.
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- One pot synthesis of 5-(substituted aryl) methyl-4,5,6,7-tetrahydrothieno [3,2-c] pyridine using chloromethyl methyl ether
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Ticlopidine and its analogues were prepared by one pot synthesis without isolating the intermediates. This sequential one pot synthesis avoided a lengthy separation process, workup and purification of the intermediate compounds and thus could save the time and resources and increased the yield.
- Rege, Chandana M.,Gadre,Bhalekar, Satish M.
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p. 197 - 198
(2013/09/23)
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- Method of making thieno-pyridine derivatives
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The present invention provides a method of preparing thieno[3,2-c]pyridine derivatives of formula I: wherein R1 is selected from the group consisting of lower alkyl; lower alkylene phenyl; substituted lower alkylene phenyl wherein the phenyl is substituted from 1 to 3 times with lower alkyl, lower alkoxy, lower acyloxy, hydroxy, nitro and halo; lower alkylene naphthyl, lower alkylene thienyl; lower alkylene diphenyl; lower alkylene-hydroxy-phenyl; substituted lower alkylene-hydroxy-phenyl wherein the phenyl is substituted from 1 to 3 times with lower alkyl, lower alkoxy, lower acyloxy, hydroxy, nitro, and halo; lower alkylene-hydroxy-naphthyl; lower alkylene-hydroxy-thienyl; lower alkylene-hydroxy-diphenyl, and R2 is H or lower alkylene. The method comprises reacting a compound of a formula II: with a cyclic dioxy or cyclic dithio in the presence of catalyst.
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- A modified Mannich reaction using 1,3-dioxolane
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Mannich reaction of ketones using 1,3-dioxolane instead of formaldehyde, paraformaldehyde, or 1,3,5-trioxane afforded the corresponding Mannich bases in high yields. Under the same conditions the aminomethylation of aromatics did not proceed but the intramolecular aminomethylation, like a Pictet-Spengler type reaction, proceeded smoothly.
- Sumita,Koumori,Ohno
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p. 1676 - 1678
(2007/10/02)
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- Preparation of 2-(2-thienyl) ethylamine and synthesis of thieno [3,2-C] pyridine derivatives therefrom
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Compounds of the formulae:and wherein:, R1, R2, R3 and R4 are independently hydrogen, lower alkyl of one to six carbon atoms, aryl or substituted aryl;, are advantageously converted to isocyanurate compounds, 2-(2-thienyl)ethylamine compounds and thieno[3,2-c]pyridine derivatives and the pharmaceutically acceptable salts thereof, particularly ticlopidine hydrochloride.
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- 2-thienylglycidic derivative, process for its preparation and its use as synthesis intermediate
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The invention relates to isopropyl 2-thienylglycidate of formula: STR1 obtained by reaction of 2-thienylcarboxaldehyde with an isopropyl haloacetate. It is employed as a synthesis intermediate in the preparation of 2-thienylacetaldoxime and of medications derived from thieno[3,2-c]pyridine.
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- Carbamate salts of 2-(2'-thienyl)alkylamines
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The carbamate salt of 2-(2'-thienyl)-alkylamines and particularly the ethylamine and its method of synthesis are disclosed. The carbamate salt of 2-(2'-thienyl)ethylamine is a stable, easily transportable crystalline material that can be converted to 2-(2'-thienyl)ethylamine, a useful intermediate in the synthesis of 5[(2-chlorophenyl)methyl]-4,5,6,7-tetrahydrothieno-[3,2-c]pyridine hydrochloride, also known as ticlopidine hydrochloride. The synthesis is carried out by reacting an amine of formula (I): STR1 with CO2 in a hydrocarbon solvent to obtain the carbamate salt of formula II: STR2
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- 2-(2-nitrovinyl)thiophene reduction and synthesis of thieno[3,2-c]pyridine derivatives
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An improved process for the reduction of 2-(2-nitrovinyl)thiophene to form 2-(2-thienyl)ethylamine employs a boron-containing reducing agent, preferably diborane. The 2-(2-thienyl)ethylamine produced by this process is advantageously converted to ticlopidine.
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- Process for the preparation of thienopyridine derivatives
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This invention relates to a process for the preparation of compounds having the general formula: STR1 in which: R1 represents a hydrogen atom, an optionaly substituted alkyl, aryl or aralkyl radical; R2 and R3 are the same or different and represent independently a hydrogen atom, a lower alkyl, aryl or heterocyclic radical; and R4 represents a hydrogen atom or an alkyl, cycloalkyl, alkoxy carbonyl, carboxy, aryl or heterocyclic radical, comprising reacting a compound having the formula: STR2 in which R1, R2 and R3 are as defined above, with a compound having the formula: STR3 in which R4 is as defined above; X is a halogen atom, or an optionally substituted alkoxy, thioalkyl or amino group; and Y represents an optionally substituted alkoxy, thioalkyl or amino group, or a group of the formula: STR4 in which R is a lower alkyl or aryl radical; or both the groups X and Y, together with the carbon atom to which they are attached, form a 6-membered hexahydro-S-triazinic, trioxannic or trithianic heterocyclic nucleus, in an inert solvent, at a temperature between 0° and 150° C. and in an anhydrous medium, and, if desired, liberating the free base.
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