THE TITLE COMPOUND [SYSTEMATIC NAME: N-methyl-3-(1-naphth-yloxy)-3-(2-thien-yl)propan-1-aminium chloride], C(18)H(20)NOS(+)·Cl(-), was crystallized from 1,4-dioxane. Twofold rotational disorder exhibited by the thio-phene ring in a 0.580 (5):0.420 (5) ratio represents two different conformations of the mol-ecule that exist in the same crystal form. The crystal structure contains strong N-H⋯Cl hydrogen bonds.
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http://dx.doi.org/10.1107/S1600536809033996 | DOI Listing |
Acta Crystallogr E Crystallogr Commun
April 2023
Mark Wainwright Analytical Centre, The University of New South Wales, UNSW, Sydney NSW 2052, Australia.
Duloxetine hydro-chloride (trade name Cymbalta) is marketed as a single enanti-omer ()--methyl-3-(naphthalen-1-yl-oxy)-3-(thio-phen-2-yl)propyl-am-in-ium chloride, CHNOS·Cl, which is twice as effective as the ()-enanti-omer in serotonin uptake. Here, we report the crystal structure of duloxetine hydro-chloride in its racemic form (space group 2), where it shows significant differences in the mol-ecular conformation and packing in its extended structure compared to the previously reported ()-enanti-omer crystal structure. Mol-ecules of this type, comprising aromatic groups with a single side chain terminated in a protonated secondary amine, are commonly found in active anti-depressants.
View Article and Find Full Text PDFTHE TITLE COMPOUND [SYSTEMATIC NAME: N-methyl-3-(1-naphth-yloxy)-3-(2-thien-yl)propan-1-aminium chloride], C(18)H(20)NOS(+)·Cl(-), was crystallized from 1,4-dioxane. Twofold rotational disorder exhibited by the thio-phene ring in a 0.580 (5):0.
View Article and Find Full Text PDFActa Crystallogr Sect E Struct Rep Online
February 2008
The title compound, C(19)H(21)NOS, is an inter-mediate for the synthesis of duloxetine hydro-chloride. In the mol-ecular structure, the thio-phene and naphthalene ring systems make a dihedral angle of 87.5°.
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