Synthesis and biological properties of 2-hydroxy-1-(1-phenyltetralyl)piperidine and some of its intermediates as derivatives of phencyclidine.

Abstract

Phencyclidine (1-(1-phenylcyclohexyl)piperidine, CAS 956-90-1, PCP) has shown analgesic effects. Some of its derivatives were synthesized and their biological properties were studied. To date, only saturated ketones have been used as starting materials for synthesizing the phencyclidine family. In order to show desirable biological activity, the aromatic and piperidine rings are necessary for these compounds. Using alpha-tetralone as a starting material, 2-hydroxy-1-(-phenyltetralyl)piperidine, an analogue of the phencyclidine family, and some of its intermediates were synthesized. This ketone was reacted with phenyl magnesium bromide and the resultant alcohol was reacted with acetic anhydride to give alkene that was treated with potassium permanganate to give diol. This compound was treated with a suspension of sodium azide and trichloroacetic acid to give the azide compound that was reduced with LiAlH4 to give the primary amine. Cyclization of this compound with 1,5-dibromopentane finally gave a tertiary amine. It is predicted that the title compound 2-hydroxy-1-(1-phenyltetralyl)piperidine exerts a potent analgesic effect on acute and phasic pain.

• Authors: Abbas Ahmadi, Ali Mahmoudi
• Journal: Arzneimittel-Forschung (Arzneimittelforschung) Vol. 55 Issue 9 Pg. 528-32 ( 2005) ISSN: 0004-4172 [Print] Germany
• PMID: 16229117 (Publication Type: Journal Article)

Chemical References

• 2-hydroxy-1-(1-phenyltetralyl)piperidine
• Analgesics
• Indicators and Reagents
• Piperidines
• Phencyclidine

Topics

• Analgesics (chemical synthesis)
• Indicators and Reagents
• Magnetic Resonance Spectroscopy
• Mass Spectrometry
• Phencyclidine (analogs & derivatives, chemical synthesis)
• Piperidines (chemical synthesis)
• Spectrophotometry, Infrared