(2S,3S,5R)-2-(3,5-Difluorophenyl)-3,5- dimethyl-2-morpholinol:  A Novel Antidepressant Agent and Selective Inhibitor of Norepinephrine Uptake

Synthesis and Characterization of in Vitro and in Vivo Profiles of Hydroxybupropion Analogues: Aids to Smoking Cessation

“…After stirring for 20 min at 0 °C, the reaction mixture was concentrated to a pink oil residue. Column chromatography on silica gel using CH 2 Cl 2 as the eluent afforded 9.15 g (77%) of 14 as a light pink oil with characterization data as previously reported:32 [α]25 D +40.5° (c 1.0, CHC1 3 ); 1 H NMR (CDCl 3 ) δ 5.27 (q, 1H, J = 6.9 Hz), 3.85 (s, 3H), 1.71 (d, 3H, J = 6.9 Hz); 13 C NMR (CDCl 3 ) δ 167.8, 79.9, 53.3, 18.0; LCMS (ESI) m/z 240.1 [(M + 4H) + , M = C 5 H 7 F 3 O 5 S].…”

“…Analogues 4n, 4p, 5 , and 6 were synthesized as racemic mixtures by following the standard synthesis of bupropion analogues,25 except substituting 2-amino-2-methyl-1-propanol for t -butylamine, shown in Scheme 2. As illustrated in Scheme 2, the appropriate propiophenones ( 8l–o ) were first synthesized by the addition of ethylmagnesium bromide to the nitriles ( 7 ), or in the case of the 3-pyridyl analogue was synthesized by lithium halogen exchange starting with 3-bromopyridine ( 11 ) and adding proprionitrile.…”

Enantiomeric Determination of the Phenylmorpholinol Metabolite of Bupropion in Human Plasma Using Coupled Achiral-Chiral Liquid Chromatography

“…1). (Earlier studies had depicted the chemical structure of 2 to be that of a noncyclic hydroxy ketone, but subsequently was reported to be the phenylmorpholinol (Kelley et al, 1996).) Other major metabolites include the erythro and threo amino alcohols (3 and 4) formed by the reduction of (rac) 1.…”

Heterocycles via intramolecular platinum-catalyzed propargylic substitution

“…The 1,4-morpholine unit is prevalent in nature and is featured in compounds with a range of functions including antidepressant, 4 antiparasitic, 5 anti-tumor, 6 antioxidant, 7 and anti-inflammatory 8 activities. 9 Over 100 compounds listed in the world drug index contain a morpholine subunit.…”