Collect. Czech. Chem. Commun.
1994, 59, 675-682
https://doi.org/10.1135/cccc19940675
Preparation of Racemic cis- and trans-2-(2-Alkoxyphenylcarbamoyloxy)cycloheptylmethylpiperidinium Chlorides
Fridrich Gregáňa, Viktor Kettmannb, Pavol Novomeskýb and Július Sivýb
a Department of Organic and Inorganic Chemistry, Faculty of Pharmacy, Comenius University, 832 32 Bratislava, Slovak Republic
b Department of Analytical Chemistry, Faculty of Pharmacy, Comenius University, 832 32 Bratislava, Slovak Republic
Abstract
The synthesis of two pairs of the title diastereomers, which represent conformationally constrained analogues of the phenylcarbamate local anesthetics, is described. The synthesis was accomplished by starting from cycloheptanone and 2-alkoxyanilines and the intermediate diastereomers of 2-aminomethylcycloalkanols (VI, VII) were separated as their 4-nitrobenzoyl derivatives (IV, V) by extraction and fractional crystallization. The prepared compounds (VIIIa, VIIIb, IXa, and IXb) are assumed to be of help in interpreting the structure activity relationships within this class of drugs.
