Applications of 5-Amino-1-pentanol

5-Amino-1-pentanol is a soluble white crystal that must be stored in a tight container and placed in a cool, dry place. 5-Amino-1-pentanol is toxic and prone to burns, avoids direct contact, does not come into contact with oxidants, acids, air and carbon dioxide, and is present in mainstream smoke.

Fig 1. Chemical structure formula and three-dimensional structure of 5-Amino-1-pentanol

5-Amino-1-pentanol(5-AP) is an aliphatic amino alcohol with potential plasma lipid-lowering properties. 5-Amino-1-pentanol and other amino alcohols are used as emulsifying agents in dry-cleaning soaps, wax removers, cosmetics, paints and insecticides. 5-Amino-1-pentanol undergoes facile intramolecular cyclocondensation to piperidine and to methyl or ethyl piperidines in the presence of methanol or ethanol over zeolite catalysts like ZSM5 (Si/A1 = 30, 129, 280), HM and HY. 2-Aminopyran (2-AP) is also observed as a major product in the conversion of 5-Amino-1-pentanol to piperidine on the ZSM-5 (280) and HY. Piperidine and N-methylpiperidine are predominantly formed over HY zeolite with near total conversion (98%) of 5-Amino-1-pentanol in the 5-Amino-1-pentanol alkylation with methanol. 2-Methyl piperidine is also formed as a side product in this reaction over all the zeolites studied. Methanol conversion does not show any trend. 5-amino- 1 -pentanol has been shown to be an effective process for the preparation of saturated pyridine bases over zeolite catalysts.The selectivity to piperidine and 2-aminopyran depends on the type of zeolite used. 350℃ is the best temperature for the maximum conversion of 5-Amino-1-pentanol and high yield of piperidine and N-methylpiperidine on the various zeolites employed in the reaction[1]. 

5-Amino-1-pentanol can be used as a saccharification and amination intermediate for many drugs due to both hydroxyl and amino groups, and more and more are used in the synthesis of anticancer drugs and antiinflammatory drugs. 5-Amino-1-pentanol has a wide range of applications in drug modification and drug screening. 5-Amino-1-pentanol is the starting material for the synthesis of alkaloid manzamine. 5-Amino-1-pentanol has been used in the synthesis of S-glycosyl amino-acid building blocks. It has been used as starting reagent in the synthesis of aminofunctionalized 4-chloro-2,2′:6′,2′′-terpyridine.

References

[1] Reddy B N , Kulkarni S J , Subrahmanyam M . Zeolite catalysed intramolecular cyclization of 5-amino-1-pentanol to piperidine bases[J]. Applied Catalysis. A: General, 1994, 119(1):23-32