Phenoxyphenylpiperidines
AssigneeAmerican Hoechst Corporation
InventorsHelen H. Ong, James A. Profitt
Life of this patent
Estimating the term…
Abstract
Novel phenoxyphenylpiperidines and methods of preparing same are described. These compounds are useful as analgetics, antidepressants, anticonvulsants and intermediates for preparing other pharmaceutically active compounds.
Claims74
A compound of the formula ##STR19## or a pharmaceutically acceptable acid addition salt thereof in which R is hydrogen, loweralkyl, loweralkenyl, loweralkynyl, cycloalkylloweralkyl, phenylloweralkyl, loweralkanoyl, phenoxycarbonyl, aminocarbonyl, benzoylloweralkyl, cyano, ethylene glycol ketal of the formula ##STR20## or tetrahydrofurylmethyl;
- R' is cyano, COOH, COZ, loweralkylcarbonyl or loweralkoxycarbonyl;
- X and Y are the same or different and each can be hydrogen, chlorine, fluorine, bromine, methoxy, methylthio or trifluoromethyl;
- Z is chlorine, fluorine or bromine;
- m and m' are the same or different and each can be the integer 1 or 2;
- and n is an integer of from 1 to 4, inclusive.
A process for preparing a compound of the formula ##STR22## in which X and Y are the same or different and each can be hydrogen, chlorine, fluorine, bromine, methoxy, methylthio or trifluoromethyl and m and m' are the integer 1 or 2 which comprises treating a compound of the formula ##STR23## in which Y, X, m and m' are as defined earlier with mechlorethamine hydrochloride in the presence of a base at a temperature ranging from ambient to about 85.degree. C.
A process for preparing a compound of the formula ##STR24## in which X and Y are the same or different and each can be hydrogen, chlorine, fluorine, bromine, methoxy, methylthio or trifluoromethyl and m and m' are the integer 1 or 2 which comprises treating a compound of the formula ##STR25## according to the first step of the von Braun reaction including a solvent such as chloroform or methylene chloride, a mild acid scavenger such as potassium carbonate and a reaction temperature ranging from about ambient to reflux as reaction conditions.
A process for preparing a compound of the formula ##STR26## in which X and Y are the same or different and each can be hydrogen, chlorine, fluorine, bromine, methoxy, methylthio or trifluoromethyl and m and m' are the integer 1 or 2 which comprises subjecting to acid hydrolysis a compound of the formula ##STR27##
A process for preparing a compound of the formula ##STR28## in which X and Y are the same or different and each can be hydrogen, chlorine, fluorine, bromine, methoxy, methylthio or trifluoromethyl and m and m' are the integer 1 or 2 and R is loweralkanoyl which comprises acylating a compound of the formula ##STR29## with an appropriate alkanoyl halide or alkanoylanhydride.
A process for preparing a compound of the formula ##STR30## in which X and Y are the same or different and each can be hydrogen, chlorine, fluorine, bromine, methoxy, methylthio or trifluoromethyl;
- m and m' are the integer 1 or 2;
- and R is loweralkanoyl which comprises subjecting to displacement a compound of the formula ##STR31## with an appropriate acid halide.
A process for preparing a compound of the formula ##STR32## in which X and Y are the same or different and each can be hydrogen chlorine, fluorine, bromine, methoxy, methylthio or trifluoromethyl;
- m and m' are the integer 1 or 2;
- and R' is loweralkanoyl which comprises treating a compound of the formula ##STR33## with a Grignard reagent of the formula R"Mghal in which R" is straight or branched chain loweralkyl and hal is bromine or chlorine under Grignard reaction conditions.
A process for preparing a compound of the formula ##STR34## in which X and Y are the same or different and each can be hydrogen, chlorine, fluorine, bromine, methoxy, methylthio or trifluoromethyl;
- m and m' are the integer 1 or 2;
- and R' is loweralkanoyl which comprises treating a compound of the formula ##STR35## according to the first step of the von Braun reaction including a solvent such as chloroform or methylene chloride, a mild acid scavenger such as potassium carbonate and a reaction temperature ranging from about ambient to reflux as reaction conditions.
A process for preparing a compound of the formula ##STR36## in which X and Y are the same or different and each can be hydrogen, chlorine, fluorine, bromine, methoxy, methylthio or trifluoromethyl;
- m and m' are the integer 1 or 2;
- R' is loweralkanoyl or CN which comprises subjecting to hydrolysis a compound of the formula ##STR37##
A process for preparing a compound of the formula ##STR38## in which X and Y are the same or different and each can be hydrogen, chlorine, fluorine, bromine, methoxy, methylthio or trifluoromethyl;
- m and m' are the integer 1 or 2;
- R is hydrogen or CN;
- and R' is loweralkoxycarbonyl which comprises esterifying a compound of the formula ##STR39## in which X, Y, m, m' and R are as defined earlier and R' is COZ in which Z is OH, chlorine, bromine or fluorine.
A process for preparing a compound of the formula ##STR40## in which X and Y are the same or different and each can be hydrogen, chlorine, fluorine, bromine, methoxy, methylthio or trifluoromethyl;
- m and m' are the integer 1 or 2;
- R is loweralkyl, loweralkynyl, tetrahydrofurylmethyl, cycloalkylloweralkyl, phenylloweralkyl or ethylene glycol ketal of the formula ##STR41## R' is loweralkanoyl or loweralkoxycarbonyl;
- and n is an integer between 1 and 4, inclusive, which comprises alkylating a compound of the formula ##STR42## with an appropriate alkylating agent.
A process for preparing a compound of the formula ##STR43## in which X and Y are the same or different and each can be hydrogen, chlorine, fluorine, bromine, methoxy, methylthio or trifluoromethyl;
- m and m' are the integer 1 or 2;
- and R' is loweralkanoyl or loweralkoxycarbonyl which comprises subjecting to acid hydrolysis a compound of the formula ##STR44##
A process for preparing a compound of the formula ##STR45## in which X and Y are the same or different and each can be hydrogen, chlorine, fluorine, bromine, methoxy, methylthio or trifluoromethyl;
- m and m' are the same or different and each can be the integer 1 or 2;
- R is hydrogen, loweralkyl, loweralkenyl, loweralkynyl, cycloalkylloweralkyl, phenylloweralkyl, loweralkanoyl, benzoylloweralkyl, cyano, ethylene glycol ketal of the formula ##STR46## or tetrahydrofurylmethyl;
- and R' is loweralkanoyl or loweralkoxycarbonyl which comprises treating a compound of the formula ##STR47##
A process for preparing a compound of the formula ##STR48## in which X and Y are the same or different and each can be hydrogen, chlorine, fluorine, bromine, methoxy, methylthio or trifluoromethyl;
- m and m' are the same or different and each can be the integer 1 or 2;
- R is loweralkyl, loweralkenyl, loweralkynyl, cycloalkylloweralkyl, phenylloweralkyl, loweralkylcarbonyl, benzoylloweralkyl, cyano, ethylene glycol ketal of the formula ##STR49## or tetrahydrofurylmethyl;
- and R' is COO loweralkyl which comprises esterifying a compound of the formula ##STR50##
Dependencies are inferred from the claim text.