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Crystal and Molecular Structures of Two Antiarrythmic alfa-[(Diarylmethoxy) methyl]-1-piperidineethanols

Kubicki M.

Polish Journal of Chemistry

2001

Vol. 75, nr 9

1361-1366

The crystal structures of two antiarrythmic piperidineethanols, _-{[(2-methylphenyl) phenylmethoxy]methyl}-2,6-dimethyl-1-piperidineethanol (1) and _-[(bis(2,6-dimethylphenyl) methoxy)methyl]-2,6-dimethyl-1-piperidineethanol (2) have been determined by X-ray structure analysis of single crystals. The piperidine rings are close to ideal chair conformations, the methyl substituents are in equatorial positions. Overall shapes of the molecules differ significantly: in compound 1 the oxygen atoms are in anti position, while in 2 their mutual disposition is gauche. Dihedral angles between the phenyl rings and C-O-C plane are close to 90_ for the mono- or di-substituted phenyl rings, while for the unsubstituted phenyl ring in 1 this value is smaller, equals 27.8(3)_. The bond angles in phenyl rings are influenced by the presence of methyl substituents. In both crystal structures the molecules make centrosymmetric dimers connected by strong O-H___N hydrogen bonds (piperidine nitrogen atoms act as acceptors).