Process for producing piperidine derivatives by degrading quaternary piperidinium salts

Abstract

Abstract 1. A PROCESS FOR PRODUCING A PIPERIDINE COMPOUND OF THE FORMULA, 1-((R4,R5-PHENYL)-CO-CH2-CH2-CH2-),4-(R3,R1-PHENYL-), 4-R1-PIPERIDINE WHEREIN R1 IS HYDROXY, ALKYL HAVING UP TO 4 CARBON ATOMS, ALKOXY HAVING UP TO 4 CARBON ATOMS, ALKANOYL HAVING UP TO 5 CARBON ATOMS, ALKANOYLOXY HAVING UP TO 5 CARBON ATOMS, CARBOXY, ALKOXYCARBONYL HAVING UP TO 5 CARBON ATOMS CARBAMOYL, N-(C1-C3 ALKYL)CARBAMOYL, N-DI (C1-C3 ALKYL)CARBAMOYL, N-(C1-C4 ALKANOYL)AMINOMETHYL OR N-(C1-C4 ALKOXYCARBONYL)AMINOMETHYL; R2 AND R3 ARE RESPECTIVELY HYDROGEN, HYDROXY, ALKYL HAVING UP TO 4 CARBON ATOMS, ALKOXY HAVING UP TO 4 CARBON ATOMS, HALOGEN OR TRIFLUORIMETHYL; R4 IS HYDROGEN, HALOGEN, NITRO OR (C1-C4) ALKANOYLAINO AND R5 IS HALOGEN, WHICH COMPRISES DEGRADING A QUASTERNARY PIPERIDINIUM SALT OF THE FORMULA, 1-((R5,R4-PHENYL)-C(=Z)-CH2-CH2-CH2-),1-R,4-R1,4-(R2,R3- PHENYL-)-PIPERIDINIUM X(-) WHEREIN R IS BENZYL OR 2-PHENETHYL; X IS HALOGEN; Z IS OXYGEN OR ETHYLENEDIOXY; AND R1, R2, R3, R4 AND R5 ARE AS DEFINE ABOVE, AND IN CASE WHERE Z IS ETHYLENEDIOXY, HYDROLYZING THE RESULTING KETAL COMPOUND OF THE FORMULA, 1-((2-(R4,R5-PHENYL-)-1,3-DIOXOLAN-2-YL)-CH2-CH2-CH2-), 4-R1,4-(R2,R3-PHENYL-)-PIPERIDINE WHEREIN R1, R2, R3, R4 AND R5 ARE AS DEFINE ABOVE, TO REGENERATE THE CARBONYL FUNCTION.

Inventors

• 👤 M Nakao
• 👤 M Takayama
• 👤 S Katayama
• 👤 K Sasajima
• 👤 I Maruyama
• 👤 S Inaba
• 👤 H Yamamoto
• 👤 Y Tanaka
• 👤 J Katsube
• 👤 K Ono
• 👤 I Yanagihara

Bibliographic Details