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Details for Patent: 6,399,778

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Details for Patent: 6,399,778

Title: Synthesis of 3-[4-(2-aminoethoxy)-benzoyl]-2-aryl-6-hydroxybenzo[b]thiophenes
Abstract:The present invention is directed to chemical processes for preparing 2-aryl-6-hydroxy-3-[4-(2-aminoethoxy)benzoyl]benzo[b]-thiophenes. The present invention is also directed to crystalline solvates and a non-solvated crystalline form of 6-hydroxy-2-(4-hydroxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]-benzo[b]th iophene hydrochloride, as well as processes for their preparation.
Inventor(s): LaBell; Elizabeth Smith (Lafayette, IN), McGill; John McNeill (Lafayette, IN), Miller; Randal Scot (Lafayette, IN)
Assignee: Eli Lilly and Company (Indianapolis, IN)
Filing Date:Jun 06, 1995
Application Number:08/469,093
Claims:1. A process for preparing a crystalline solvate of a compound of the formula: ##STR14##

which comprises:

a) acylating a benzothiophene of the formula: ##STR15##

wherein:

R.sup.4 is C.sub.1 -C.sub.4 alkoxy; and

R.sup.5 is C.sub.1 -C.sub.4 alkyl;

with an acylating agent of the formula: ##STR16##

wherein:

R.sup.6 is chloro, bromo, or hydroxyl;

in the presence of a solvent and boron trichloride;

b) dealkylating the acylated benzothiophene by reacting said acylated benzothiophene with additional boron trichloride to prepare a compound of the formula: ##STR17##

c) isolating the crystalline solvate.

2. The process of claim 1 wherein R.sup.6 is chloro.

3. The process of claim 2 wherein R.sup.4 is methoxy and R.sup.5 is methyl.

4. The process of claim 3 wherein the acylation is conducted in the presence of 2-5 molar equivalents of BCl.sub.3.

5. The process of claim 3 wherein the dealkylation is conducted in the presence of 3-10 molar equivalents of BCl.sub.3.

6. The process of claim 3 where in the solvent is 1,2-dichlorethane.

7. A process for preparing a crystalline solvate of the formula: ##STR18##

which comprises the process of claim 1 wherein the solvent is 1,2,3-trichloropropane and which further comprises the step of adding methanol to the product mixture of step b) prior to isolating the crystalline solvate.

8. The process of claim 7 wherein R.sup.4 is methoxy, and R.sup.5 is methyl.

9. A process for preparing a crystalline solvate of the formula: ##STR19##

which comprises the process of claim 1 wherein the solvent is 1,2-dichloroethane and which further comprises the step of adding methanol to the product mixture of step b) prior to isolating the crystalline solvate.

10. The process of claim 9 wherein R.sup.4 is methoxy, and R.sup.5 is methyl.
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