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Generated: July 27, 2017

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Title: Process for the preparation of derivatives of piperidine
Abstract:Processes for the preparation of the antiarrhythmic agent 2,5-bis(2,2,2-trifluoroethoxy)-N-(2-piperidylmethyl)benzamide.
Inventor(s): Leir; Charles M. (New Richmond, WI)
Assignee: Riker Laboratories, Inc. (St. Paul, MN)
Filing Date:Sep 04, 1985
Application Number:06/772,474
Claims:1. A method of preparing a 2,5-bis(2,2,2-trifluoroethoxy)-N-(2-piperidylmethyl)-benzamide which comprises:

(a) contacting 1,4-dibromobenzene with an alkali metal 2,2,2-trifluoroethoxide in the presence of cuprous or cupric ion and in a strongly polar solvent comprising 2,2,2-trifluoroethanol whereby 1,4-bis(2,2,2-trifluoroethoxy)benzene is formed;

(b) in the presence of a Lewis acid catalyst, treating said 1,4-bis(2,2,2-trifluoroethoxy)benzene with an acetylation agent under conditions to create 2,5-bis(2,2,2-trifluoroethoxy)acetophenone:

(c) replacing the methyl moiety of the acetophenone function of said 2,5-bis(2,2,2-trifluoroethoxy)acetophenone to yield 2,5-bis(2,2,2-trifluoroethoxy)benzoic acid;

(d) treating said 2,5-bis(2,2,2-trifluoroethoxy)benzoic acid with an inorganic chloride to provide 2,5-bis(2,2,2-trifluoroethoxy)benzoic acid chloride;

(e) contacting the resultant 2,5-bis(2,2,2-trifluoroethoxy)benzoic acid chloride with 2-aminomethylpyridine, whereby there is formed 2,5-bis(2,2,2-trifluoroethoxy)-N-(2-pyridylmethyl)benzamide;

(f) treating said 2,5-bis(2,2,2-trifluoroethoxy)-N-(2-pyridylmethyl)benzamide with an agent capable of hydrogenation of the aromatic bond in the heterocyclic ring, whereby there is formed a 2,5-bis(2,2,2-trifluoroethoxy)-N-(2-piperidylmethyl)benzamide.

2. A method of claim 1 wherein said 2,5-bis(2,2,2-trifluoroethoxy)-N-(2-piperidylmethyl)benzamide is recovered in the form of its acetate.

3. A method of preparing a 2,5-bis(2,2,2-trifluororethoxy)-N-(2-piperidylmethyl)benzamide which comprises:

(a) contacting 1,4-dibromobenzene with an alkali metal 2,2,2-trifluoroethoxide in the presence of cuprous or cupric ion and in a strongly polar solvent comprising 2,2,2-trifluoroethanol to yield 1,4-bis(2,2,2-trifluoroethoxy)benzene;

(b) in the presence of a Lewis acid catalyst, treating said 1,4-bis(2,2,2-trifluoroethoxy)benzene with an acetylation agent under conditions to create 2,5-bis(2,2,2-trifluoroethoxy)acetophenone;

(c) replacing the methyl moiety of the acetophenone function of said 2,5-bis(2,2,2-trifluoroethoxy)acetophenone using hypochlorite to yield 2,5-bis(2,2,2-trifluoroethoxy)benzoic acid;

(d) treating said 2,5-bis(2,2,2-trifluoroethoxy)benzoic acid with an inorganic chloride to provide 2,5-bis(2,2,2-trifluoroethoxy)benzoic acid chloride;

(e) contacting the resultant 2,5-bis(2,2,2-trifluoroethoxy)benzoic acid chloride with 2-aminomethylpiperidine, whereby there is formed 2,5-bis(2,2,2-trifluoroethoxy)-N-(2-piperidylmethyl)benzamide.

4. A method of claim 3 wherein said 2,5-bis(2,2,2-trifluoroethoxy)-N-(2-piperidylmethyl)benzamide is recovered in the form of its acetate.
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