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N-Phenylcyclohexylamine. Formula: C 12 H 17 N. Molecular weight: 175.2701. IUPAC Standard InChI: InChI=1S/C12H17N/c1-3-7-11 (8-4-1)13-12-9-5-2-6-10-12/h1,3-4,7-8,12-13H,2,5-6,9-10H2. Copy Sheet of paper on top of another sheet.
The present study describes the synthesis of three substituted 1-(1-phenylcyclohexyl)piperidines, (3-MeO-, 4-MeO- and 3-Me-PCP) and three substituted 1-(1-phenylcyclohexyl)pyrrolidine analogues (3-MeO-, 4-MeO- and 3-Me-PCPy).
Cyclohexylamine is produced by two routes, the main one being the complete hydrogenation of aniline using some cobalt- or nickel-based catalysts: [4] C 6 H 5 NH 2 + 3 H 2 → C 6 H 11 NH 2. It is also prepared by alkylation of ammonia using cyclohexanol.
[1-Phenylcyclohexyl]piperidine (Phencyclidine, PCP, I) is a noncompetitive antagonist of the NMDA (N-methyl-Daspartate) subcategory of the glutamate receptor that leads to the release and decrease of reabsorbing of monoaminergic neurotransmitters such as dopamine, serotonin, and norepinephrine [1].
Synthesis of PCP from PCA via 1-phenylcyclohexanol (PCOH) The PCOH starting material can be purchased or prepared by reaction of phenyllithium or phenyl grignard with cyclohexanone. This alcohol is then be transformed into the amine by reaction with sodium azide (~90% yield) followed by reduction.
Even though PCP was the first synthesized arylcyclohexylamine, other compounds had been reported before. For example, 1-(1-phenylcyclohexylamine)amine (PCA) was first stated in 1907, in 1953 N-ethyl-1-phenylcyclohexylamine (PCE) was investigated, and 1-(1-Phenylcyclohexyl) morpholine (PCMo) in 1954 .
Arylcyclohexamines (also known as arylcyclohexylamines) are a group of compounds that contain a cyclohexamine unit with an aryl moiety, typically a phenyl ring, attached to the same atom to which the amine group is linked (see Fig. 1).