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Details for Patent: 7,390,906

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Details for Patent: 7,390,906

Title:Piperidine derivatives and process for their production
Abstract: The present invention relates to substantially pure piperidine derivative compounds of the formulae: ##STR00001## wherein R.sub.1 is hydrogen or hydroxy; R.sub.2 is hydrogen; or R.sub.1 and R.sub.2 taken together form a second bond between the carbon atoms bearing R.sub.1 and R.sub.2; R.sub.3 is --COOH or --COOR.sub.4; R.sub.4 has 1 to 6 carbon atoms; A, B, and D are the substituents of their respective rings each of which may be different or the same and are hydrogen, halogens, alkyl, hydroxy, alkoxy, or other substituents. A process of preparing such piperidine derivative compounds in substantially pure form is also disclosed.
Inventor(s): D'Ambra; Thomas E. (Wynantskill, NY)
Assignee: AMR Technology, Inc. (Manchester, VT)
Filing Date:Jun 19, 2006
Application Number:11/455,531
Claims:1. A process of preparing a piperidine derivative compound of the formula: ##STR00042## wherein R.sub.1 is hydrogen or hydroxy; R.sub.2 is hydrogen; or R.sub.1 and R.sub.2 taken together form a second bond between the carbon atoms bearing R.sub.1 and R.sub.2; R.sub.3 is --COOH or --COOR.sub.4; R.sub.4 has 1 to 6 carbon atoms; said process comprising: providing a regioisomer of the following formula: ##STR00043## converting the regioisomer to the piperidine derivative compound with a piperidine compound of the formula: ##STR00044##

2. A process according to claim 1, wherein said providing comprises: acylating a starting compound of the formula: ##STR00045## wherein R.sub.5 is OR.sub.6, --N(R.sub.6).sub.2, and --SR.sub.6, and R.sub.6 is an alkyl with 1 to 6 carbons, with a compound of the formula: ##STR00046## wherein X is a halogen, under conditions effective to produce a first mixture of regioisomers of the formula: ##STR00047## hydrolyzing the first mixture of regioisomers under conditions effective to form a second mixture of a regioisomers of the formula: ##STR00048## recovering from the second mixture of regioisomers the regioisomer of the formula: ##STR00049##

3. A process according to claim 2, wherein said recovering comprises: crystallizing from the second mixture of regioisomers a regioisomer salt of the formula: ##STR00050## wherein X.sup.+ is a Lewis Acid; isolating the regioisomer salt; and converting the regioisomer salt to the regioisomer of the formula: ##STR00051##

4. A process according to claim 3, wherein X.sup.+ is an alkali metal salt or an ammonium salt of the form NR.sub.7R.sub.8R.sub.9 wherein R.sub.7, R.sub.8, and R.sub.9 are individually hydrogen or a straight or branched alkyl of 1 to 6 carbon atoms, or an alkyl substituted at any position with a phenyl ring or a substituted phenyl ring.

5. A process according to claim 2, wherein said acylating is carried out by a Friedel-Crafts reaction using AlCl.sub.3 catalyst.

6. A process according to claim 1, further comprising: reducing the piperidine derivative under conditions effective to form a hydroxylated piperidine derivative of the formula: ##STR00052##

7. A process according to claim 6, wherein the hydroxylated piperidine derivative has the formula: ##STR00053##

8. A process according to claim 1, wherein said converting comprises: halogenating the regioisomer of the following formula: ##STR00054## under conditions effective to form a first intermediate compound of the formula: ##STR00055## wherein X is a halogen and reacting the first intermediate compound with a piperidine compound of the formula: ##STR00056## under conditions effective to form the piperidine derivative of the following formula: ##STR00057##

9. A process according to claim 1, wherein said converting comprises: reacting the regioisomer of the following formula: ##STR00058## with a piperidine compound of the formula: ##STR00059## under conditions effective to form the piperidine derivative of the formula: ##STR00060##
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