Synthesis of anabaseine, salts and derivatives thereof
US5530134A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Sep 6, 1994 |
| Grant date | Jun 25, 1996 |
| Priority date | — |
| Expiry date | Sep 6, 2014 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D213/50
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
A process for the synthesis of compounds of the formulas Ia and Ib below, wherein R.sub.1, R.sub.2, and R.sub.3, which are the same or different, are each selected from hydrogen and C.sub.1 -C.sub.4 alkyl, including the compound Anabaseine (Ia, wherein R.sub.1 =R.sub.2 R.sub.3 =H) (3,4,5,6-tetrahydro-2', 3'-bipyridine), the process comprising reacting sodium salt of .delta.-valerolactone with substituted ethyl nicotinate derivative to produce the Claisen product sodium 3-nicotinoyl-2-tetrahydropyranone enolate derivative, heating the sodium 3-nicotinoyl-2-tetrahydropyranone enolate derivative with concentrated HCl to produce 3-(5-chloro-1-pentanone-1-yl) pyridine derivative, dissolving the 3-(5-chloro-1-pentanone-1-yl) pyridine derivative in ethanol and then heating the 3-(5-chloro-1-pentanone-1-yl) pyridine derivative in ethanol with ethanolic ammonia solution in a sealed container to produce the compound Ia. Also, the process steps in the above process, and the products and intermediate products produced thereby. ##STR1##
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.