A new synthesis of 1-arylpiperidin-4-ols
- 31 December 1987
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 10,p. 2881-2885
- https://doi.org/10.1039/p19880002881
Abstract
1,5-Dichloropentan-3-ol (8), which is readily prepared from the corresponding ketone (7), reacts with 2-fluoro-, 4-methyl-, 2-chloro-, 3-chloro-, 4-chloro-, and 3-chloro-4-methyl-anilines in the presence of potassium carbonate and sodium iodide in dimethylformamide at 100 °C to give 1-(2-fluorophenyl)-, 1-(4-tolyl)-, 1-(2-chlorophenyl)-, 1-(3-chlorophenyl)-, 1-(4-chlorophenyl)-, and 1-(3-chloro-4-tolyl)piperidin-4-ols, respectively. The (2-fluorophenyl)-, (4-tolyl)-, and (4-chlorophenyl)-piperidin-4ols are converted into the corresponding 1-arylpiperidin-4-ones. 1-(2-Fluorophenyl)piperidin-4-one (10; R1= F, R2= R3= H) is converted into its dimethyl acetal (12) and thence into the enol ether (13).This publication has 0 references indexed in Scilit: