Verfahren zur Herstellung neuer Aroylalkyl- und Hydroxyaralkylderivate von 4-(N-Arylalkanamido)-piperidinen und verwandter Verbindungen

摘要

The invention comprises compounds of the formula (wherein Ar is phenyl, halophenyl, tolyl, methoxy-phenyl or thienyl; X is -CO-, -CHOH- or -CHO (lower alkanoyl)-; Alk is methylene, ethylene, propylene or lower alkylidene; R is lower alkyl, cyclopropyl, phenyl, lower alkoxy, dimethylamino, morpholino, 1-piperidinyl or 1-pyrrolidinyl; and R1 is hydrogen, methyl or methoxy; the word lower referring to radicals containing less than 7 carbon atoms) and their preparation by condensing a compound of the formula Ar-CO-alk-halogen with a compound of the formula to form a compound of the formula and, if desired, reducing this to the corresponding secondary alcohol, or if the secondary alcohol wherein -alkis methylene is required, reacting styrene oxide with a compound of the Formula II, and, if desired, acylating the secondary alcohols. Examples are given, and salts with inorganic and organic acids and quaternary ammonium derivatives with organic esters of sulphuric, hydrohalic and aromatic sulphonic acids are described. Piperidine derivatives of the Formula II are prepared by condensing 1-benzyl-4-piperidone with appropriate amines to give compounds of the formula reducing these to compounds of the formula reacting these with appropriate anhydrides, alkyl chloroformates or phosgene (to form amides of chloroformic acid) and then secondary amines to give compounds of the formula and subjecting these to hydrogenolysis to remove the benzyl group.