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• W2099799946 abstract "The 1H NMR spectrum (CD2Cl2) of the mesylate analogue of phendimetrazine bitartarate, a central nervous system stimulant and an anorexic drug, showed two isomers (ratio ≈︁ 17:1) differing in the stereochemistry of the N+HCH3 moiety. A similar diastereomeric ratio was also noted in 13C{1H} NMR spectra recorded in either CD2Cl2 or in acidic D2O (pD ≈︁ 1). For the major species in CD2Cl2 solution, four antiperiplanar vicinal 1H1H coupling constants indicated a chair-conformation 2,3-trans-1,4-oxazine ring with equatorially oriented 2-phenyl, 3-methyl and N-methyl substituents. The minor species also has the same chair conformation with equatorially oriented 2-phenyl and 3-methyl substituents, since the coupling constant for the minor species vicinal OCH(Ph)CH(Me)N methine protons was also antiperiplanar in magnitude. Axial N-methyl stereochemistry was assigned to the minor species, since chemical shifts of the ring carbons gauche to N-methyl (and of the N-methyl carbon atom itself) were shifted characteristically upfield relative to absorbances for the corresponding carbons in the major [equatorial N-methyl] species. The R-factor method was used to estimate an OC6C5N dihedral angle of 56.0(7)° for the major equatorial N-methyl species in CD2Cl2 solution. CP-MAS 13C NMR chemical shifts for solid-state phendimetrazine bitartarate are the same as those for the solution-state equatorial N-methyl diastereomer. The oxydimethyleneaminomethyl fragment in the equatorial N-methyl phendimetrazine chair conformation was used as a model for the corresponding fragment in the eight-membered ring of nefopam. Comparison of OCH2CH2N+H(equatorial CH3)— and OCH2CH2N+H vicinal coupling constants in the two rings suggests dynamic weighted averaging for those in the octagonal ring of the nefopam equatorial NCH3 diastereomer." @default.
• W2099799946 created "2016-06-24" @default.
• W2099799946 creator A5053438967 @default.
• W2099799946 date "1989-12-01" @default.
• W2099799946 modified "2023-09-25" @default.
• W2099799946 title "1H and13C NMR studies on the oxydimethyleneaminomethyl fragment in six- and eight-membered rings. The solution stereochemistry ofN-methyl diastereomers of phendimetrazine (an oxazine anorexic drug)versus nefopam (a benzoxazocine analgesic drug)" @default.
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• W2099799946 doi "https://doi.org/10.1002/mrc.1260271207" @default.
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