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Generated: December 16, 2017

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Title: Process for the preparation of intermediates of derivatives of pyrrolidine and piperidine
Abstract:An improved process for the preparation of certain antiarrhythmic agents in which a carbon atom of a piperidine or pyrrolidine ring is bonded directly or through a methylene group to the nitrogen of a substituted benzamido group from bromo- or hydroxy-substituted benzenes.
Inventor(s): Leir; Charles M. (New Richmond, WI)
Assignee: Riker Laboratories, Inc. (St. Paul, MN)
Filing Date:Jul 28, 1986
Application Number:06/890,821
Claims:1. A method of preparing 2,5-bis(2,2,2-trifluoroethoxy)benzoic acid comprising:

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

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

(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.

2. A method of preparing 2,5-bis(2,2,2-trifluoroethoxy)benzoic acid chloride comprising:

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

(b) treating said 1,4-bis(2,2,2-trifluoroethoxy)benzene, in the presence of a Lewis acid catalyst, 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; and

(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.

3. A method of preparing 2,5-bis(2,2,2-trifluoroethoxy)-N-(2-pyridylmethyl)benzamide comprising:

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

(b) treating said 1,4-bis(2,2,2-trifluoroethoxy)benzene, in the presence of a Lewis acid catalyst, 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; and

(e) contacting said 2,5-bis(2,2,2trifluoroethoxy)benzoic acid chloride with 2-aminomethylpyridine to provide 2,5-bis(2,2,2-trifluoroethoxy)-N-(2-pyridylmethyl)benzamide.
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