244223-89-0Relevant academic research and scientific papers
A low-waste process to sertraline by diastereomeric crystal resolution and waste isomer racemisation
Blacker, A. John,Brown, Stuart,Clique, Blandine,Gourlay, Brian,Headley, Catherine E.,Ingham, Stephen,Ritson, Dougal,Screen, Thomas,Stirling, Matthew J.,Taylor, David,Thompson, Gary
, p. 1370 - 1378 (2009)
A semi-continuous method for recovering waste sertraline isomers from a diastereomeric crystallisation process is described in which the mother liquors from a highly selective mandelic acid resolution for the (1S,4S) isomer are treated sequentially with S
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 (2004)
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.
Resolution of sertraline with (R)-mandelic acid: Chiral discrimination mechanism study
He, Quan,Rohani, Sohrab,Zhu, Jesse,Gomaa, Hassan
scheme or table, p. 119 - 128 (2012/03/27)
The chiral discrimination mechanism in the resolution of sertraline with mandelic acid was investigated by examining the weak intermolecular interactions (such as hydrogen bond, CH/π, and van der Waals interactions) and molecular packing difference in crystal structures of the resulting diastereomeric salts. A new one-dimensional chain-like hydrogen-bonding network and unique supramolecular packing mode are disclosed. The investigation demonstrated that stable hydrogen-bonding pattern, herringbone-like arrangement of aromatic rings, and planar boundary surface in the hydrophobic region are the three most important structural characteristics expected in less soluble diastereomeric salts. The existence and magnitude of hydrogen bond, CH/π interaction, and van der Waals interaction related to three characteristic structures, determine the stability of diastereomeric salt. The hydrogen bond is not necessarily the dominant factor while the synergy and optimization of all weak intermolecular interactions attribute to the chiral recognition.
AN IMPROVED PROCESS FOR THE MANUFACTURE OF SERTRALINE
-
Example 1, (2010/08/04)
A process for preparing (±)-cis-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1- naphthalenamine (sertraline) and/or a pharmaceutically acceptable acid addition salt thereof comprising hydrogenation of 4-(3,4-dichlorophenyl)-3,4-dihydro-N-methyl-1- naphthalenimine (sertraline-1-imine) in the presence of a polar solvent using palladium / alumina as a catalyst at a temperature ranging from 25°C to 35°C to obtain (±)-cis/trans- sertraline with the (±)-cis racemate of sertraline as the major product.
Resolution of Racemic Organic Acids with (1S, 4S)-4[3,4-Dichlorophenyl]-1,2,3,4-Tetrahydro-N-Methyl-1-Naphthaloneamine
-
Page/Page column 3, (2009/10/18)
The present invention relates to novel chiral resolving agents and a process for resolution of racemic organic acids and their derivatives of the formula (+, ?)—R1R2CHCOOR3 with Cis-(1S,4S)-4[3,4-dichlorophenyl]-1,2,3,4-tetrahydro-N-methyl-1-naphthaloneamine and its Cis-(1R,4R)-isomer as well as Trans-(1S,4R)-4[3,4-dichlorophenyl]-1,2,3,4-tetrahydro-N-methyl-1-naphthaloneamine and its Trans-(1R,4S)-isomer.
Novel processes for preparing sertraline hydrochloride crystalline forms
-
Page/Page column 3, (2008/06/13)
The present invention discloses novel and improved processes for preparation of sertraline hydrochloride crystalline form II. Thus, for example, sertraline free base is dissolved in isoamyl alcohol at 25-30° C., pH of the mass is adjusted to 2.0 with conc. hydrochloric acid (36%) at 25-30° C. and then stirred for 14 hours at 25-30° C. Filtered the solid and dried at 65° C. for 4 hours to give sertraline hydrochloride crystalline form II. The present invention also provides a novel process for preparation of sertraline hydrochloride crystalline form I.
IMPROVED MANUFACTURING PROCEDURE FOR THE PREPARATION OF POLYMORPHIC FORM II OF CIS-(1S)-N-METHYL-4-(3,4-DICHLOROPHENYL)-1,2,3,4-TETRAHYDRO-1-NAPTHLENEAMINE HYDROCHLORIDE (SERTRALINE HYDROCHLORIDE)
-
Page/Page column 24, (2008/06/13)
The present invention relates to the improved, scalable and efficient manufacturing procedure for the preparation of the antidepressant Cis-(1S)-N-Methyl-4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-1-napthaleneamine hydro chloride, Sertraline Hydrochloride polymorphic form II. The present invention further relates to the improved and modified procedures for preparing, separating and isolating the key intermediates involved in the preparationof Sertraline Hydrochloride polymorphic form II. The present invention also further relates to the use of novel reagents or a combination thereof and new methodologies to prepare some o'f the key intermediates involved in the preparation of Polymorphic Form II of Sertraline Hydrochloride.
A HIGHLY STEREOSELECTIVE SYNTHESIS OF SERTRALINE
-
Page/Page column 12-13, (2010/11/25)
The present invention relates to a process for highly stereoselective synthesis of sertraline and sertraline intermediate. Thus, the mixture of 4-(3,4-Dichlorophenyl)-3,4-dihydro-N-methyl-1(2H)-naphthalenimine, 5 % Pd/CaCO3, water and methanol is taken in a hydrogenation flask and then subjected to hydrogenation under a hydrogen pressure of 0.5 Kg at 20 - 35°C for 3 hours 30 minutes. The catalyst is removed by filtration and the solvent is evaporated completely under vacuum to obtain cis-(±)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-naphthalen amine. (trans-(±): 0.2).
PROCESSES FOR PREPARING SERTRALINE
-
Page/Page column 26, (2008/06/13)
Provided are processes for the preparation of sertraline and sertraline hydrochloride.
PROCESSES FOR THE PREPARATION OF SERTRALINE HYDROCHLORIDE
-
Page/Page column 10-12, (2008/06/13)
The invention relates to processes for the preparation of Schiff's base, and to the use of Schiff's base as intermediate in the preparation of naphthalenamine derivatives which are active compounds for treating the anxiety related disorders. The invention also relates to processes for the preparation of sertraline or a pharmaceutically acceptable salt thereof, and pharmaceutical compositions that include the sertraline.
