Preparation of Racemic cis- and trans-2-(2-Alkoxyphenylcarbamoyloxy)cycloheptylmethylpiperidinium Chlorides

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Title:Preparation of Racemic cis- and trans-2-(2-Alkoxyphenylcarbamoyloxy)cycloheptylmethylpiperidinium Chlorides
Creators:
Gregáň, Fridrich
Kettmann, Viktor
Novomeský, Pavol
Sivý, Július
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 59, 3, pp. 675-682

Abstract

<p>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 (<i>VI</i>, <i>VII</i>) were separated as their 4-nitrobenzoyl derivatives (<i>IV</i>, <i>V</i>) by extraction and fractional crystallization. The prepared compounds (<i>VIIIa</i>, <i>VIIIb</i>, <i>IXa</i>, and <i>IXb</i>) are assumed to be of help in interpreting the structure activity relationships within this class of drugs.

Title:Preparation of Racemic cis- and trans-2-(2-Alkoxyphenylcarbamoyloxy)cycloheptylmethylpiperidinium Chlorides
Creators:
Gregáň, Fridrich
Kettmann, Viktor
Novomeský, Pavol
Sivý, Július
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:59
Number:3
Page Range:pp. 675-682
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19940675UNSPECIFIED
ID Code:490
Item Type:Article
Deposited On:06 Feb 2009 17:01
Last Modified:06 Feb 2009 16:01

Citation

Gregáň, Fridrich; Kettmann, Viktor; Novomeský, Pavol; Sivý, Július (1994) Preparation of Racemic cis- and trans-2-(2-Alkoxyphenylcarbamoyloxy)cycloheptylmethylpiperidinium Chlorides. Collection of Czechoslovak Chemical Communications, 59 (3). pp. 675-682. ISSN 0010-0765

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