1-Benzyl-4-chloromethylpiperidine: A Building Block in the Synthesis of Compounds of Pharmacological Interest

Abstract

The first synthesis of 1-benzyl-4-(chloromethyl)piperidine (1) is described, together with its application in the synthesis of potential pharmaceuticals. Reaction of 1 with several purines in basic medium proceed through the initial formation of 1-benzyl-1azoniabicyclo[2.2.1]heptane system, which then undergoes nucleophilic attack at two different carbons, yielding N-benzylpiperidine and N-benzylpyrrolidine derivatives.

A New Tacrine–Melatonin Hybrid Reduces Amyloid Burden and Behavioral Deficits in a Mouse Model of Alzheimer’s Disease

“…Our study is based on the work of Rodriguez-Franco's group in the field of AD (Martinez et al 2000;Rodríguez-Franco et al 2001Rodríguez-Franco and Fernández-Bachiller 2002) focuses on dual acting drugs, capable of combining AChE inhibition and antioxidant properties in a single small molecule. They have developed this new tacrine-melatonin hybrid, which is a potent inhibitor of human AChE and shows a high oxygen radical absorbance capacity (Rodríguez-Franco et al 2006;Fernández-Bachiller et al 2009).…”

Complete assignment of the 1H and 13C NMR spectra of some N‐benzyl‐(piperidin or pyrrolidin)‐purines

“…1). 3 Both show complex 1 H NMR spectra, and we describe here their complete spectroscopic characterization, including both the 1 H and 13 C chemical shifts and 1 H, 1 H coupling constants.…”

Synthesis of New 1-(But-2-ynyl)pyrazoles: Containing a Pyrrolidine or Diethylamine Moiety and Their Muscarinic Properties

“…1,2,4-thiadiazolidinones, imidazoles, and pyrazoles) that display acetylcholinesterase inhibition [8][9][10] or muscarinic properties [11,12], now we are interested in the synthesis of new oxotremorine-like compounds derived from pyrazoles and pyrrolidine or diethylamine ( Figure 1, general formula I) as potential muscarinic agents. 1,2,4-thiadiazolidinones, imidazoles, and pyrazoles) that display acetylcholinesterase inhibition [8][9][10] or muscarinic properties [11,12], now we are interested in the synthesis of new oxotremorine-like compounds derived from pyrazoles and pyrrolidine or diethylamine ( Figure 1, general formula I) as potential muscarinic agents.…”