Background
Many piperidine derivatives have multiple pharmacological activities such as antibacterial, antitumor, treatment of Alzheimer's disease and anesthesia. They are also important drugs for the treatment of viral infections (including AIDS) and diabetes. 3-Hydroxypiperidine or its derivatives are one of the important intermediates, which are widely used in the synthesis of drug intermediates such as chiral 3-aminopiperidine. It is of great significance to develop a synthesis method suitable for industrial production.
Chemical Properties
White to light yellow crystalline powder and lumps
Application
3-Hydroxypiperidine may be used to synthesize the following:
2-pyrrolidinone via oxidation with iodosylbenzene
1-[2,8-bis(trifluoromethyl)quinolin-4-yl]piperidin-3-ol via reaction with 4-bromoquinoline
Reactant for:
Synthesis of unsymmetrical ureas
Synthesis of piperidine nucleoside analogs
Fluorination reactions
Synthesis of substituted pyridines
Uses
3-Hydroxypiperidine is usually used for Synthesis of unsymmetrical ureas,Synthesis of piperidine nucleoside analogs,Fluorination reactions,Synthesis of substituted pyridines.
General Description
3-Hydroxypiperidine can be obtained from the reduction of 3-hydroxypyridine.
Synthesis
Dissolve 86.0g of 5-bromo-2-hydroxypentylamine hydrobromide in 150mL of water, and add a solution of 60mL of water containing 15.0g of sodium carbonate at 10-15°C, and drip it for about 1 hour. After dripping, react at about 15°C for 2 hours. Then heat to 30-40°C and react for 2 hours. Stop the reaction, cool it to room temperature, and concentrate the reaction solution under reduced pressure to remove most of the water. Filter it to remove salt, wash it with cold water, and continue to concentrate the mother liquor. The crude product is distilled under reduced pressure to obtain 26.5g of colourless oily 3-hydroxypiperidine, yielding 80%.
