79560-20-6Relevant articles and documents
Development of [3]ferrocenophane-derived N/B frustrated Lewis pairs for the metal-free catalytic hydrogenation of imines
Pan, Zhentao,Wang, Hui,Ling, Fei,Xiao, Lian,Song, Dingguo,Zhong, Weihui
, p. 522 - 528 (2019/02/01)
A series of novel [3]ferrocenophane-derived N/B frustrated Lewis pairs (FLPs) were synthesized and successfully applied to the catalytic hydrogenation of imines in 71–93% yields. This approach could be easily conducted on gram scale and provided versatile synthetic route for the key intermediate of sertraline hydrochloride without heavy metal residues.
PROCESS FOR THE PREPARATION OF AN IMINE INTERMEDIATE
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Page/Page column 11-12, (2008/06/13)
The invention is directed to a process for the preparation of [4(S,R)-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalene-1-ylidene]-methyl-amine of the Formula (I) by reacting 4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)naphthalene-l-one of the Formula (II) with monomethyl amine which comprises carrying out the reaction in the presence of thionyl chloride in an ether-type solvent. The [4(S,R)-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalene-1-ylidene]-methyl-amine of the Formula I is a valuable pharmaceutical intermediate.
A new and simplified process for preparing N-[4-(3,4-dichlorophenyl)-3,4- dihydro-1(2H)-naphthalenylidene]methanamine and a telescoped process for the synthesis of (1S-cis)-4-(3,4-dichlorophenol)-1,2,3,4-tetrahydro-N-methyl-1- naphthalenamine mandelate: Key intermediates in the synthesis of sertraline hydrochloride
Taber, Geraldine P.,Pfisterer, David M.,Colberg, Juan C.
, p. 385 - 388 (2013/09/05)
N-[4-(3,4-Dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]-methanamine, sertraline imine (3), is an intermediate for the synthesis of Zoloft, sertraline hydrochloride (1). A cleaner, simpler, and more efficient alternative to the Schiff base-mediated formation of sertraline imine has been developed and is presented in this paper. The condensation reaction between 4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalone, sertraline tetralone (2), and monomethylamine was carried out in ethanol, without the need for classical dehydrating agent, such as TiCl4, or more novel approaches, such as molecular sieves, both of which produce hazardous byproducts and solid wastes. The low solubility of the imine 3 in this type of solvent is exploited, such that the reaction equilibrium favorably enhances the imine formation. Furthermore, an improved and highly selective catalytic reduction of 3 with Pd/CaCO3 catalyst in ethanol as the reaction solvent, followed by the resolution of the racemic cis isomer (6) with D-(-)-mandelic acid results in a more efficient telescoped commercial process to (1S-cis)-4-(3,4-dichlorophenol)- 1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine mandelate, sertraline mandelate (4). This new process has been implemented commercially and eliminates the use of hazardous material such as TiCl4, significantly reduces undesirable byproducts, reduces the number of intermediate isolations, and improves the overall process yield and productivity on industrial scale.