N,O-Dimethyl-4-(2-naphthyl)piperidine-3-carboxylate

Introduction

N,O-Dimethyl-4-(2-naphthyl)piperidine-3-carboxylate is a chemical compound that belongs to the class of piperidine derivatives. It is commonly used in the field of organic chemistry as a building block for the synthesis of various pharmaceuticals and other organic compounds. This article aims to provide a detailed overview of N,O-Dimethyl-4-(2-naphthyl)piperidine-3-carboxylate, including its chemical structure, properties, synthesis, and applications.

Chemical Structure

The chemical structure of N,O-Dimethyl-4-(2-naphthyl)piperidine-3-carboxylate consists of a piperidine ring with a carboxylate group attached to the third carbon atom. Additionally, there is a 2-naphthyl group attached to the fourth carbon atom of the piperidine ring. The nitrogen atom of the piperidine ring is also substituted with two methyl groups. The molecular formula of N,O-Dimethyl-4-(2-naphthyl)piperidine-3-carboxylate is C19H21NO2.

File:N,O-Dimethyl-4-(2-naphthyl)piperidine-3-carboxylate.png

Chemical structure of N,O-Dimethyl-4-(2-naphthyl)piperidine-3-carboxylate

Properties

N,O-Dimethyl-4-(2-naphthyl)piperidine-3-carboxylate is a white to off-white crystalline solid. It has a melting point of approximately 120-125°C. The compound is sparingly soluble in water but soluble in organic solvents such as ethanol, methanol, and dichloromethane. It exhibits moderate stability under normal conditions and should be stored in a cool, dry place away from light and moisture.

Synthesis

The synthesis of N,O-Dimethyl-4-(2-naphthyl)piperidine-3-carboxylate involves several steps. One common method involves the reaction of 2-naphthylamine with 1,3-dibromopropane to form 4-(2-naphthyl)piperidine. This intermediate is then reacted with dimethyl carbonate and a base, such as potassium carbonate, to yield N,O-Dimethyl-4-(2-naphthyl)piperidine-3-carboxylate. The reaction typically takes place under reflux conditions and requires careful control of temperature and reaction time.

Applications

N,O-Dimethyl-4-(2-naphthyl)piperidine-3-carboxylate finds applications in various fields, particularly in the synthesis of pharmaceutical compounds. It serves as a versatile building block for the preparation of diverse piperidine-based drugs, including antipsychotics, analgesics, and anti-inflammatory agents. The compound's unique structural features make it an attractive starting material for the development of new drug candidates with improved pharmacological properties.

Safety Considerations

When handling N,O-Dimethyl-4-(2-naphthyl)piperidine-3-carboxylate, it is important to follow proper safety precautions. The compound may cause skin and eye irritation, and inhalation of its dust or vapors should be avoided. It is recommended to use appropriate protective equipment, such as gloves and goggles, when working with this compound. In case of accidental exposure or ingestion, medical attention should be sought immediately.

See Also

• Piperidine
• Organic Chemistry
• Pharmaceuticals