Abstract
An improved method for the synthesis of 3-quinuclidinone hydrochloride 4 from piperidine-4-carboxylic acid 1 has been described. Reaction of piperidine-4-carboxylic acid 1 with thionyl chloride and ethanol gave ethyl piperidine 4-carboxylate 2. It was further condensed with methyl chloroacetate in presence of sodium carbonate to give ethyl 1-(2-methoxy-2- oxoethyl)piperidine-4-carboxylate 3. One pot Dieckmann reaction of 3 in presence of potassium tertbutoxide followed by hydrolysis and decarboxylation gave title compound azabicyclo[2.2.2]oct-3-one hydrochloride 4.
Keywords: 3-quinuclidinone hydrochloride, Dieckmann reaction, isonepecotic acid, Gram scale synthesis.
Letters in Organic Chemistry
Title:An Improved and Simple Route for the Synthesis of 3-Quinuclidinone Hydrochloride
Volume: 12 Issue: 4
Author(s): Jigar Y. Soni, V. Premasagar and Sonal Thakore
Affiliation:
Keywords: 3-quinuclidinone hydrochloride, Dieckmann reaction, isonepecotic acid, Gram scale synthesis.
Abstract: An improved method for the synthesis of 3-quinuclidinone hydrochloride 4 from piperidine-4-carboxylic acid 1 has been described. Reaction of piperidine-4-carboxylic acid 1 with thionyl chloride and ethanol gave ethyl piperidine 4-carboxylate 2. It was further condensed with methyl chloroacetate in presence of sodium carbonate to give ethyl 1-(2-methoxy-2- oxoethyl)piperidine-4-carboxylate 3. One pot Dieckmann reaction of 3 in presence of potassium tertbutoxide followed by hydrolysis and decarboxylation gave title compound azabicyclo[2.2.2]oct-3-one hydrochloride 4.
Export Options
About this article
Cite this article as:
Soni Y. Jigar, Premasagar V. and Thakore Sonal, An Improved and Simple Route for the Synthesis of 3-Quinuclidinone Hydrochloride, Letters in Organic Chemistry 2015; 12 (4) . https://dx.doi.org/10.2174/1570178612666150113231048
DOI https://dx.doi.org/10.2174/1570178612666150113231048 |
Print ISSN 1570-1786 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6255 |
- Author Guidelines
- Graphical Abstracts
- Fabricating and Stating False Information
- Research Misconduct
- Post Publication Discussions and Corrections
- Publishing Ethics and Rectitude
- Increase Visibility of Your Article
- Archiving Policies
- Peer Review Workflow
- Order Your Article Before Print
- Promote Your Article
- Manuscript Transfer Facility
- Editorial Policies
- Allegations from Whistleblowers
Related Articles
-
MicroRNAs: Emerging Role in the Endogenous μ Opioid System
CNS & Neurological Disorders - Drug Targets Specific Immune Intervention with Monoclonal Antibodies for the Treatment of Multiple Sclerosis
Current Medicinal Chemistry Hybrids of Coumarin Derivatives as Potent and Multifunctional Bioactive Agents: A Review
Medicinal Chemistry Synthesis of New Galanthamine-Peptide Derivatives Designed for Prevention and Treatment of Alzheimer’s Disease
Current Alzheimer Research Antimicrobial and Cell-Penetrating Peptides: Structure, Assembly and Mechanisms of Membrane Lysis via Atomistic and Coarse-Grained Molecular Dynamic Simulations
Protein & Peptide Letters Alpha-1 Antitrypsin Deficiency: Current Perspective from Genetics to Diagnosis and Therapeutic Approaches
Current Medicinal Chemistry Beta-Blockers use for Hypertension in the Elderly
Cardiovascular & Hematological Agents in Medicinal Chemistry Different Regulation Modes of Calcineurin Regulatory Subunit on Its Catalytic Subunit with RII Peptide and Tau as Substrates
Protein & Peptide Letters Influence of Phenobarbital on Morphine Metabolism and Disposition:LC-MS/MS Determination of Morphine (M) and Morphine-3-Glucuronide (M3G) in Wistar-Kyoto Rat Serum, Bile, and Urine
Current Drug Metabolism Why Antidiabetic Vanadium Complexes are Not in the Pipeline of “Big Pharma” Drug Research? A Critical Review
Current Medicinal Chemistry PET Tracers for Serotonin Receptors and Their Applications
Central Nervous System Agents in Medicinal Chemistry Non-Imidazole Histamine H3 Ligands. Part VI. Synthesis and Preliminary Pharmacological Investigation of Thiazole-Type Histamine H3-Receptor Antagonists with Lacking a Nitrogen Nucleus in the Side Chain
Medicinal Chemistry Diagnosis, Treatment, and New Developments in Preeclampsia
Current Women`s Health Reviews Editorial (Application of a Multidisciplinary Approach to Alzheimers Disease to Develop Novel Drug Targets by Integrating Biomarkers, Imaging, Genetic and Molecular Strategies)
Current Alzheimer Research G Protein-Coupled Receptor Signaling Complexity in Neuronal Tissue:Implications for Novel Therapeutics
Current Alzheimer Research Role of Gut Microbiota in Obesity, Type 2 Diabetes and Alzheimer’s Disease
CNS & Neurological Disorders - Drug Targets Inhibition of Pancreatic Ribonuclease A Aggregation by Antibodies Raised Against the Native Enzyme and Its N-Terminal Dodecapeptide
Protein & Peptide Letters β-Secretase as a Therapeutic Target for Inhibitor Drugs
Current Medicinal Chemistry Vascular Risk Factors and Alzheimer’s Disease Pathogenesis: Are Conventional Pharmacological Approaches Protective For Cognitive Decline Progression?
CNS & Neurological Disorders - Drug Targets Are Human Tyrosinase and Related Proteins Suitable Targets for Melanoma Therapy?
Current Topics in Medicinal Chemistry