PREPARATION OF RACEMIC CIS AND YPHENYL-CARBAMOYLOXY)CYCLOHEPTYLMETHYLPIPERIDINIUM CHLORIDES

The synthesis of two pairs of the title diastereomers, which represent conformationally constrained analogues of the phenylcarbamate local a nesthetics, is described. The synthesis was accomplished by starting f rom cycloheptanone and 2-alkoxyanilines and the intermediate diasterco mers of 2-amino-methylcycloalkanols (VI, VII) were separated as their 4-nitrobenzoyl derivatives (IV, V) by extraction and fractional crysta llization. The prepared compounds (VIIIa, VIllb, IXa, and IXb) are ass umed to be of help in interpreting the structure-activity relationship s within this class of drugs.