The crystal and molecular structure ofdl-betaprodine hydrochloride

Abstract

The crystal structure of the hydroehloride of d/-betaprodine (fl-dl. 1,3-dimethyl-4-phenyl-4-propionoxypiperidine) has been determined from a three-dimensional vector convergence map. The atomic parameters have been refined by Fourier and differential syntheses to an R index of 0.096 for 2108 observed reflections, and all the hydrogen atoms in the structure have been located from a difference map. The betaprodine molecule in the monoclinic crystals of the hydrochloride has the same configuration and conformation as in the orthorhombic crystals of the hydrobromide. In both cases, the piperidine ring has the chair form with the phenyl ring equatorial and the propionoxy chain axial as in the alpha isomer, but the methyl group on C(3) is axial and is cis to the phenyl ring on C(4) in the betaprodine molecule.

The crystal structure of pascoite, Ca3V10O28.16H2O

“…The complete structure-factor table, based on the parameters listed in Tables 1 and 2, has been deposited in the National Science Library of Canada at the National Research Council, Ottawa. A summary of the agreement between IFol and IFcl (Ahmed & Barnes, 1963a), however, is presented in Table 3 where it may be noted that only four reflections (all unobserved) out of 4238 examined show relatively high discrepancies.…”

Structural studies of synthetic analgetics. IV. The crystal and molecular structure of (+-)-α-promedol alcohol

“…Some of the relevant structural features of the isomeric promedol alcohols (De Camp & Ahmed, 1972a, c, d), and the isomers of prodine HC1 (Kartha, Ahmed & Barnes, 1960;Ahmed & Barnes, 1963) are summarized in Table 4. The analgetic potency of the promedol alcohols and their esters is in the order y< ~ <fl, and that of the prodines is ct<fl (Casy & McErlane, 1971).…”

Quantum chemical calculations of flexible opiate narcotics: Methadone, meperidine, and prodines

“…, and ( -) B [9] prodines are all in a phenyl-equatorial conformer, there was a tendency to believe that because of its greater similarity to morphine, an axial conformer was implicated at the receptor [lo] and that the lower its energy the more potent the drug [ll]. The recent synthesis of active 4-phenyl piperidine analogues constrained to be in a. phenyl-equatorial position has altered such hypotheses [ 121.…”

“…Despite the fact that crystal structures indicate that protonated meperidine [7], ( + ) a [S], and ( -) B [9] prodines are all in a phenyl-equatorial conformer, there was a tendency to believe that because of its greater similarity to morphine, an axial conformer was implicated at the receptor [lo] and that the lower its energy the more potent the drug No conformational studies of 4-phenyl piperidine compounds exist to further explore the general question of similarities between morphine, meperidine, and prodines in their low energy conformers. Methadone, as shown in Figure 5, has a central carbon atom (C,) to which are attached two phenyl rings-a COC2H, carbonyl group and a CH,CH(CH,) N(CH,), amine group.…”