Studies of the elimination of 1,2,-diaryl-4-dimethylaminobutan-2-ols—I

Thermal decomposition of propoxyphene during GLC analysis

“…The present data were nearly identical to those of Casy et al (25). Structures IV and V, respectively, fit the NMR and mass spectra.…”

“…Several investigators overcame the problem by chemical modification of propoxyphene to the corresponding carbinol (17)(18)(19). This compound is stable under normal GLC conditions but decomposes in the presence of cyanogen bromide (24) or in acidic solution (25). The acetoxy analog also decomposes in cyanogen bromide, and the structures of the resulting products were determined (24).…”

Structural influences upon antihistamine activity; 3-amino-1-aryl-1-(2-pyridyl)propenes and related compounds

“…The liberated free base mixtures were acidified with ethanolic oxalic acid and fractional crystallization produced either pure salts or isomer mixtures (pmr evidence). The remaining carbinols were dehydrated using an acetic acid and concentrated hydrochloric acid mixture according to the method of Casy, Myers & Pocha (1966 The pure oxalate of cis IX could not be isolated but its pmr characteristics were noted from various mixed oxalate crops (see Table 1). Liberation of the bases from these samples and reacidification with ethanolic hydrogen bromide led to the isolation of a 50 : 50 mixture (pmr integral data) of the cis and trans IX dihydrobromides, m.p.…”

Stereochemical influences upon antihistamine activity. Further studies of isomeric 4-amino-1, 2-diarylbutenes

“…4-Amino-1 ,2-diarylbutenes. The butan-2-01 I11 hydrochlorides were dehydrated with a mixture of acetic acid and concentrated hydrochloric acid by the previously reported method (Casy, Myers & Pocha, 1966), and the isomers in the dehydration mixture separated by fractional crystallization from ethanol-ether of the hydrohalides. Isomers are listed in their order of separation.…”