IP Library Granted Patent US 7,199,241
Granted Patent B1
US 7,199,241 · App. 11/250,343 · Granted Apr 3, 2007

Process for preparing (S) and (R)-2-[4-(4-chlorobenzhydryl)piperazin-1-yl]-ethoxyacetamide

Assignee: UCB, S.A.
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Quick Facts
Patent No.
US 7,199,241
App. No.
11/250,343
Granted
Apr 3, 2007
Kind
B1
Abstract

The present invention relates to a process for preparing (S)-2-[4-(4-chlorobenzhydryl)piperazin-1-yl]-ethoxyacetamide and (R)-2-[4-(4-chlorobenzhydryl)piperazin-1-yl]-ethoxyacetamide by separation of a racemic mixture using multiple column chromatography.

Claims (13)

1. Chromatographic process for preparing (S)-2-[4-(4-chlorobenzhydryl)piperazin-1-yl]-ethoxyacetamide and (R)-2-[4-(4-chlorobenzhydryl)piperazin-1-yl]-ethoxyacetamide, by enantiomeric resolution of 2-[4-(4-chlorobenzhydryl)piperazin-1-yl]-ethoxyacetamide, which process comprises using a system comprising series of fixed-bed columns connected in series, wherein the charge (solution of the compounds to be separated) and the eluent are injected continuously into the system while the separated compounds are removed continuously in the extract (compound most strongly retained) and the raffinate (compound least strongly retained), wherein the system comprises at least six columns filled with chiral stationary phase.

2. Process according to claim 1 , wherein the chiral stationary phase is chosen from phases based on silica gel supporting polymeric compounds.

3. Process according to claim 1 , wherein the chiral stationary phase is a phase based on silica gel supporting an ester or a carbamate of cellulose or of amylose.

4. Process according to claim 1 , wherein the system uses at least one column packed with an optical resolution packing material, said packing material consisting of silica gel supporting amylose tris(3,5-dimethylphenylcarbamate) or a chemically modified form thereof.

5. Process according to claim 4 , wherein the average particle diameter of the packing material is 1 to 300 μm.

6. Process according to claim 5 wherein the particles of the packing material are porous.

7. Process according to claim 6 , wherein the pore diameter of the particles is 10 Å–5000 Å.

8. Process according to claim 4 , wherein the amylose tris(3,5-dimethylphenylcarbamate) or chemically modified form thereof is 1 to 99% weight percent of the silica gel support.

9. Process according to claim 1 , wherein it is performed at a temperature of 5–50° C.

10. Process according to claim 1 , wherein the system comprises eight columns.

11. Process according to claim 1 , wherein the system uses an eluent an alcohol or mixture of alcohol and of alkane in a proportion (by volume) of between 50/50 and 100/0.

12. Process according to claim 1 , wherein the system uses an eluent selected from methanol, or a mixture of n-heptane and n-propanol.

13. Process according to claim 2 , wherein the polymeric compounds are selected from polysaccharide derivatives, polyacrylic derivatives and polyamide derivatives.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 21, 2008
From: UCB, S.A.
To: UCB PHARMA, S.A.
Reel/Frame 021773/0126 →
Continuity (4)
Division 1092043400 · Aug 18, 2004
Continuation 1044107300 · May 20, 2003
Continuation In Part 1021474400 · Aug 9, 2002
Continuation 0986561800 · May 29, 2001