Crystal structure and Hirshfeld surface analysis of 3-(hydroxymethyl)-3-methyl-2,6-diphenylpiperidin-4-one

Abstract

A new synthesis of the title compound, C19H21NO2, was developed with good yield and purity using the reaction of 4-hydroxy-3-methyl-2-butanone, benzaldehyde and ammonium acetate in glacial acetic acid as a solvent. The central piperidine ring adopts a chair conformation, and its least-squares basal plane forms dihedral angles of 85.71 (11) and 77.27 (11)° with the terminal aromatic rings. In the crystal, the molecules are linked by O—H...O and C—H...O hydrogen bonds into double ribbons. The Hirshfeld surface analysis shows that the most important contributions are from H...H (68%), C...H/H...C (19%) and O...H/H...O (12%) interactions.