174848-98-7

Usage

Uses

Used in Organic Synthesis:
(1S,2R)-2-(azidomethyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide is used as a precursor in organic synthesis for the generation of reactive intermediates. Its unique structure and functional groups allow for the creation of a variety of complex molecules and compounds.
Used in Chemical Research:
In the field of chemical research, (1S,2R)-2-(azidomethyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide is utilized to study the properties and reactions of cyclopropane rings, carboxamides, and azide groups. This helps in understanding the reactivity and potential applications of similar compounds.
Used in Pharmaceutical Industry:
(1S,2R)-2-(azidomethyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide is used as a potential precursor in the development of pharmaceuticals. Its unique structure and functional groups may contribute to the creation of new drugs with specific therapeutic properties.
Used in Agrochemical Industry:
In agrochemicals, (1S,2R)-2-(azidomethyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide may be employed as a starting material for the synthesis of new agrochemicals, such as pesticides or herbicides, due to its reactive intermediates and potential biological activity.
Used in Materials Science:
(1S,2R)-2-(azidomethyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide is also used in materials science for the development of new materials with specific properties. Its unique structure and functional groups can contribute to the creation of advanced materials for various applications.

Upstream product

• 140-29-4 phenylacetonitrile 
• 1001017-62-4 (1S,2R)-2-(bromomethyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide 
• 172015-99-5 (1 S,2 R)-N,N-diethyl-2-(hydroxymethyl)-1-phenylcyclopropane-carboxamide 
• 1237261-60-7 (1S,2R)-2-(chloromethyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide 
• 63106-93-4 (1S,5R)-1-phenyl-3-oxabicyclo[3.1.0]hexan-2-one 

Downstream Products

• 101152-94-7 (1S,2R)-milnacipran hydrochloride 
• 96847-54-0 (1S,2R)-2-(aminomethyl)-N,N-diethyl-1-phenylcyclopropane-1-carboxamide 

Relevant academic research and scientific papers

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.

Synthesis of enantiomerically pure milnacipran analogs and inhibition of dopamine, serotonin, and norepinephrine transporters

A series of Milnacipran analogs with variation in the aromatic moiety were prepared in high enantiomeric excess. Structure-activity relationships for two parallel enantiomeric series are described. The (-)-(1R,2S)-naphthyl analog (8h) showed the highest potency in the two series and is a triple reuptake inhibitor of the SERT, NET, and DAT.

Synthesis of (+)- and (-)-milnaciprans and their conformationally restricted analogs

Reaction of (R)-epichlorohydrin [(R)-5] and phenylacetonitrile (6) in the presence of NaNH2 in benzene gave a cyclopropane derivative which was isolated as lactone 4 [(1S,2R)-2-oxo-1-phenyl-3-oxabicyclo[3,1,0]hexane] of 96% e.e. in 67% yield, after alkaline hydrolysis of the cyano group. Compound 4 was readily converted to (+)-milnacipran [(+)-1], by which the absolute stereochemistry of (+)-1 was confirmed. (1S,2R)-1-phenyl-2-[(S)-1-aminoethyl]-cyclopropane-N,N-diethylcarboxam ides (2), a conformationally restricted analog of 1, was also synthesized in high enantiomeric purity from 4. Starting from (S)-epichlorohydrin [(S)-5], their corresponding enantiomers, namely (-)-milnacipran [(-)-1] and ent-2, were also synthesized.