cas 101152-94-7, (1R,2S)-rel-2-(Aminomethyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide hydrochloride

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An Efficient Synthesis of Milnacipran Hydrochloride via Reductive Amination of Aldehyde
An efficient synthesis of milnacipran hydrochloride has been accomplished. The important application of this paper is the reductive amination of aldehyde to primary amine with water soluble reagents. This method provides a high yield of primary amine as t
Desireddy, Neha Reddy,Glory, Arava,Bhimireddy, Krishna Reddy,Kurra, Yadagiri,Reddy, Ram
(2017)
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Preparation method of milnacipra hydrochloride intermediate
The invention provides a preparation method of an intermediate hydrochloride intermediate. Belong to chemical medicine preparation technical field. To the preparation method, the compound having the structure of the formula (II) is added into the methanol
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(2021/10/13)

Drug intermediate as well as preparation and application thereof
The invention designs a drug intermediate III, and the structural formula of the drug intermediate III is shown in the specification.
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(2021/05/08)

Preparation of leveminacipran hydrochloride
The invention discloses a novel preparation method for synthesizing leveminacipran hydrochloride, and relates to a compound represented by a formula A. According to the invention, each step of reaction is simple in operation and mild in condition, use of
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(2020/06/16)

Preparation method of 2-(aminomethyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide and salt thereof
The invention provides a novel method for preparing 2-(aminomethyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide (milnacipran) and a salt thereof. The method comprises the following steps: reducing a compound with a structure represented by a formula (I) by using a reducing agent to obtain milnacipran with a structure represented by a formula (II), and salifying milnacipran to obtain milnacipran hydrochloride. The method provided by the invention effectively controls the generation of impurities, greatly improves the yield and the purity of the product, has the characteristics of environmentalprotection, safety and economy, is suitable for industrial production, and has a wide market application prospect.
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Paragraph 0048-0050; 0051-0074

(2020/07/15)

IMPROVED PROCESS FOR THE PREPARATION OF LEVOMILNACIPRAN
The present invention discloses cost-effective, industrially efficient and safe process synthesis of levomilnacipran that is devoid of 1-phenyl-1- diethylaminocarbonyl-2- chloromethylcyclopropane.
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Page/Page column 11

(2019/06/09)

Preparation method of levomilnacipran hydrochloride
The invention relates to the field of chemical medicines and organic synthesis and in particular relates to a preparation method of levomilnacipran hydrochloride. Aiming at solving the problems of anexisting method for preparing the levomilnacipran hydrochloride that the cost is relatively high or a generation process is relatively dangerous so that large-scale industrial production is limited, the preparation method is characterized by comprising the following steps: [1] enabling phenylacetonitrile and (R)-2-chloromethyl ethylene oxide to react under the action of sodium amide to obtain a compound 1; then carrying out hydrolysis cyclization on the compound 1 to obtain a compound 2; [2] enabling the compound 2 and thionyl chloride to react in alcohol, so as to obtain a compound 3; [3] enabling the compound 3 to be subjected to exchange reaction through introducing nitryl and amino, so as to obtain a compound 6; [4] reducing nitryl in the compound 6 and forming salt in situ to obtain the levomilnacipran hydrochloride. The preparation method provided by the invention is applicable to industrial production of the levomilnacipran hydrochloride.
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(2018/09/28)

PROCESS FOR THE PREPARATION OF (1S,2R)-MILNACIPRAN
The invention relates to a process for the preparation of Levomilnacipran, a compound useful in the treatment of depression, comprising the following steps: a) directly converting the enantiomerically enriched form of alcohol (D) into the enantiomerically enriched form of the phthalimido derivative (C) by treatment with phthalimide in the presence of a trialkyl or triarylphosphine and of a dialkyl azodicarboxylate, formula (I) wherein the amount of phthalimide is comprised between 1 and 1.3 equivalents with respect to the molar amount of alcohol (D) used, and the amounts of both the phosphine and the azodicarboxylate are comprised, independently from each other, between 1 and 1.5 equivalents with respect to the molar amount of alcohol (D) used; b) deblocking the enantiomerically enriched form of the phthalimido derivative (C) to obtain Levomilnacipran, formula (II).
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(2016/06/01)

Preparation method of levomilnacipran hydrochloride
The invention provides a preparation method of levomilnacipran hydrochloride. According to the preparation method, a mixed liquid is obtained through a mixed reaction of a compound adopting the structure shown in the formula (II) and alkali; then acid is
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(2017/04/19)

Intermediate milnacipran hydrochloride and its preparation method and application
The invention relates to the technical field of synthetic methods of milnacipran hydrochloride. The preparation method provided by the invention comprises the following steps: carrying out reactions in five steps on an existing compound to generate a nove
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(2017/02/09)

PROCESS FOR PREPARING LEVOMILNACIPRAN
The present invention refers to a new process for preparing levomilnacipran, in particular to a process for the resolution of racemic tw-milnacipran with a derivative of optically active phenylglycine.
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(2015/07/07)

AN IMPROVED PROCESS FOR THE PREPARATION OF 1-ARYL 2-AMINOMETHYL CYCLOPROPANE CARBOXYAMIDE (Z) DERIVATIVES, THEIR ISOMERS AND SALTS
The present invention relates to an improved and one-pot process for the preparation of 1-Aryl 2-aminomethyl cyclopropane carboxyamide (z) derivatives, their isomers of formula (I) or its pharmaceutically acceptable salt thereof wherein R1 and R2 are represents independently selected from the group consisting of hydrogen, lower alkyl, lower aryl, and lower-alkylaryl, which aryl or alkylaryl group is optionally substituted by a halogen atom.
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(2014/02/15)

PROCESS FOR PREPARING LEVOMILNACIPRAN HCL
The invention relates to one-pot process for preparing (1S,2R)-1-phenyl-1-(N,N-diethylaminocarbonyl)-2-aminomethylcyclopropane of formula (I) comprising the step of reacting (1S,2R)-N,N-diethyl-2-(hydroxymethyl)-1-phenylcyclopropanecarboxamide successively with the following reactants 1) triethyl orthoformate and methanesulfonic acid or triethylamine and methanesulfonyl chloride, 2) a phthalimidating agent, 3) aqueous EtNH2, wherein the reaction is carried out in toluene. In another aspect the invention concerns a process for preparing (1S,2R)-N,N-diethyl-2-(hydroxymethyl)-1-phenylcyclopropanecarboxamide trough a step of crystallization of (1S,5R)-1-phenyl-3-oxabicyclo[3.1.0]hexan-2-one.
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(2014/12/09)

Asymmetric syntheses of pharmaceuticals containing a cyclopropane moiety using catalytic asymmetric Simmons-Smith reactions of allylalcohols: Syntheses of optically active tranylcypromine and milnacipran
Asymmetric synthesis of tranylcypromine was achieved using an enantioselective Simmons-Smith cyclopropanation catalyzed by a simple disulfonamide derived from an -amino acid. The optically active milnacipran was also synthesized by porcine pancreas lipase-catalyzed selective monoacylation of the C4-hydroxy group in (Z)-2-phenylbut-2-ene-1,4-diol and the enantioselective Simmons-Smith cyclopropanation as the key steps.
Ishizuka, Yuki,Fujimori, Hirohisa,Noguchi, Takuya,Kawasaki, Masashi,Kishida, Mari,Nagai, Takuya,Imai, Nobuyuki,Kirihara, Masayuki
p. 1311 - 1313
(2013/10/22)

Enantioselective synthesis of levomilnacipran
A novel approach for the asymmetric synthesis of the active (1S,2R)-enantiomer of the antidepressant milnacipran is reported. The two stereogenic centers borne by the cyclopropane ring were sequentially installed starting from phenylacetic acid.
Alliot, Julien,Gravel, Edmond,Pillon, Florence,Buisson, David-Alexandre,Nicolas, Marc,Doris, Eric
p. 8111 - 8113
(2012/09/21)

PROCESS FOR THE PREPARATION OF PHARMACEUTICALLY ACCEPTABLE SALTS OF RACEMIC MILNACIPRAN AND ITS OPTICAL ENANTIOMERS THEREOF
The present invention relates to an improved process for the preparation of pharmaceutically acceptable salts of milnacipran by mutual acid radical exchange.
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Page/Page column 8

(2012/07/28)

A NEW PROCESS FOR PREPARING OPTICALLY PURE MILNACIPRAN AND ITS PHARMACEUTICALLY ACCEPTABLE SALTS.
The present invention relates to an improved and commercially, viable process for the resolution of racemic cis milnacipran of formula I and its pharmaceutically acceptable salts of formula II. The present invention comprises using racemic cis milnacipran or its pharmaceutically acceptable salts as starting material, a low cost and commercially available resolving agent of formula III and industrially safe and economically low cost material such as water as a solvent. The said process results into optical isomers of racemic cis milnacipran having excellent optical purity without involving multiple crystallization steps. The present invention also comprises the concept of green chemistry as the invention works well with water as a solvent thereby minimizing the use of any other solvent. (Formular I and II should be inserted here) Wherein X is anion selected from Cl, Br, I, HSO4, Phosphate or organic acid(Formular III should be inserted here) *represent asymmetric centre Compound of formula III represent mandelic acid and its derivatives.
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(2012/05/20)

PROCESS FOR PREPARING OPTICALLY PURE MILNACIPRAN AND ITS PHARMACEUTICALLY ACCEPTABLE SALTS
The present invention relates to an improved and commercially, viable process for the resolution of racemic cis milnacipran of formula I and its pharmaceutically acceptable salts of formula II. The present invention comprises using racemic cis milnacipran or its pharmaceutically acceptable salts as starting material, a low cost and commercially available resolving agent of formula III and industrially safe and economically low cost material such as water as a solvent. The said process results into optical isomers of racemic cis milnacipran having excellent optical purity without involving multiple crystallization steps. The present invention also comprises the concept of green chemistry as the invention works well with water as a solvent thereby minimizing the use of any other solvent. (Formular I and II should be inserted here) Wherein X is anion selected from Cl, Br, I, HSO4, Phosphate or organic acid (Formular III should be inserted here) *represent asymmetric centre Compound of formula III represent mandelic acid and its derivatives.
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(2012/12/13)

PROCESS FOR THE PREPARATION OF (±M1R(S), 2SRR)L-2-(AMINOMETHYL)-N,N-DIETHYL-L-PHENYLCYCLOPROPANE CARBOXAMIDE HYDROCHLORIDE
The present invention relates to an improved process for the preparation of (±)-[1R(S),2S(R)]-2-(aminomethyl)-N,N-diethyl-l-phenylcyclopropane carboxamide hydrochloride compound of formula- la.
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(2012/04/23)

PROCESS FOR PREPARATION OF MILNACIPRAN INTERMEDIATE AND ITS USE IN PREPARATION OF PURE MILNACIPRAN
Disclosed is a process for the preparation of milnacipran intermediate, a compound of formula ΙII, and its use in the preparation of pure milnacipran.
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Page/Page column 26

(2012/01/06)

METHOD FOR SYNTHESIS OF (1S, 2R)-MILNACIPRAN
The present invention relates to a method for synthesizing a pharmaceutically acceptable acid addition salt of (1S, 2R)-milnacipran comprising the following successive steps: (a) reaction of phenylacetonitrile and of (R)-epichlorhydrin in the presence of a base containing an alkaline metal, followed by a basic treatment, and then by an acid treatment in order to obtain a lactone; (b) reaction of said lactone with MNEt2, wherein M represents an alkaline metal, or with NHEt2 in the presence of a Lewis acid-amine complex, in order to obtain an amide-alcohol; (c) reaction of said amide-alcohol with thionyl chloride in order to obtain a chlorinated amide; (d) reaction of said chlorinated amide with a phthalimide salt in order to obtain a phthalimide derivative; (e) hydrolysis of the phthalimide group of said phthalimide derivative in order to obtain (1S, 2R)-milnacipran, and (f) salification of (1S, 2R)-milnacipran in a suitable solvent system in the presence of a pharmaceutically acceptable acid.
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Page/Page column 16

(2010/08/09)

SOLID MILNACIPRAN AND PROCESS FOR THE PREPARATION OF THE SAME
The present invention provides novel solid milnacipran in crystalline form-G and a process for its preparation. The present invention also provides a process for the preparation of milnacipran hydrochloride from the novel solid crystalline milnacipran.
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Page/Page column 7

(2010/12/26)

A PROCESS FOR PREPARING OPTICAL PURE MILNACIPRAN AND ITS PHARMACEUTICALLY ACCEPTED SALTS
The present invention discloses a process for preparing optically pure milnacipran and their pharmaceutically acceptable salts, which adopts racemic milnacipran as starting material, tartaric acid derivatives and their compositions as resolving agents to
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Page/Page column 5-6

(2009/12/07)

A new approach towards 1-phenyl and 1-benzyl substituted 2-(aminomethyl)cyclopropanecarboxamides as novel derivatives of the antidepressant Milnacipran
2-(2-Cyano-2-phenylethyl)aziridines were converted into novel trans-2-aminomethyl-1-phenylcyclopropanecarboxamides via regiospecific ring opening and 3-exo-tet cyclisation, thus providing the first convenient entry into the trans-isomer of Milnacipran as a useful template for further derivatisation. Furthermore, unprecedented 2-aminomethyl-1- benzylcyclopropanecarboxamides have been synthesized using two different routes starting from 2-(2-cyanoethyl)aziridines, both involving α-benzylation with respect to the nitrile group and aziridine to cyclopropane ring transformation. The Royal Society of Chemistry 2009.
Vervisch, Karel,D'Hooghe, Matthias,Toernroos, Karl W.,De Kimpe, Norbert
experimental part
p. 3271 - 3279
(2009/10/24)

NOVEL POLYMORPHIC FORMS OF MILNACIPRAN HYDROCHLORIDE
The present invention relates to novel polymorphic forms of milnacipran hydrochloride. The novel polymorphic forms are designated as Form (I), Form (II), Form (III), Form (IV) and Form V of milnacipran hydrochloride. The present invention also relates to processes for the preparation of the novel polymorphic forms.
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Page/Page column 14-15

(2008/12/07)

METHOD FOR PRODUCING (Z)-1-PHENYL-1-DIETHYLAMINOCARBONYL-2-AMINOMETHYL CYCLOPROPANE HYDROCHLORIDE
The present invention provides a process for producing (Z)-1-phenyl-1-diethylaminocarbonyl-2-aminomethylcyclopropane or hydrochloride thereof, which comprises a step of reacting (Z)-1-phenyl-1-diethylaminocarbonyl-2-phthalimidomethylcyclopropane by contacting said compound with an aqueous methylamine solution having a concentration of from 1 to 25% by weight to obtain (Z)-1-phenyl-1-diethylaminocarbonyl-2-aminomethylcyclopropane.
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Page/Page column 5-6

(2008/06/13)

PROCESS FOR PRODUCING (Z)-1-PHENYL-1-(N,N-DIETHYLAMINOCARBONYL)IDOMETHYLCYCLOPROPANE
The present invention provides a process for producing (Z)-1-phenyl-1-(N,N-diethylaminocarbonyl)-2-phthalimidometh ylcyclopropane, which includes reacting (Z)-1-phenyl-1-(N,N-diethylaminocarbonyl)-2-hydroxymethylcy clopropane with an orthoester and a br?n
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Page/Page column 5

(2008/06/13)

METHOD FOR PRODUCING 2-OXO-1-PHENYL-3-OXABICYCLO[3.1.0]HEXANE
The present invention provides a process for producing 2-oxo-1-phenyl-3-oxabicyclo[3.1.0]hexane which comprises reacting phenylacetonitrile with epichlorohydrin in the presence of sodium hydride. According to the present invention, 2-oxo-1-phenyl-3-oxabicyclo[3.1.0]hexane can be produced safely, easily and industrially advantageously.
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(2008/06/13)