Diphenyl-butyrophenone

The first reported application of the technique by Kessler and Wilkinson [12] in 1981, deals with various aromatic hydrocarbons chemisorbed on Y-alumina. The samples were adsorbed at less than monolayer levels, and the transient spectra observed were shown to be due to triplet-triplet absorptions. Figure 6 shows the time resolved triplet-triplet absorption spectra obtained from 3% coverage of acridine on powdered silica [14] demonstrating the sensitivity of the method and its ability to probe acid-base reactions at catalytic surfaces. Turro and his coworkers [25,26] have studied various molecules on silica surfaces. The lifetimes of the triplet states of valerophenone and diphenyl-butyrophenone adsorbed on powdered silica were determined to be 0.3 and 0.9 [is, respectively [25] which is at least two orders of magnitude greater than in homogeneous solution. Turro et al [26] also demonstrated triplet energy transfer from benzophenone to naphthalene on silica surfaces via static and dynamic pathways. 

A mixture of 107 g (0.4 mole) of a,a-diphenyl-4-piperidinemethanol, 105 g (0.44 mole) of 4 -tert-butyl-4-chlorobutyrophenone, 70 g (0.7 mole) of potassium bicarbonate, and a small amount of potassium iodide in 600 ml of toluene was refluxed and stirred for 2.5 days then filtered. The filtrate was treated with charcoal, filtered through celite then treated with ethereal HCI. The resulting solid was recrystallized from methanol and isopropyl alcohol to give the 4 -tert-butyl-4-[4-(a-hydroxy-a-phenylbenzyl)piperidinoj-butyrophenone hydrochloride, melting point 234°-235°C. 

In our model, we have indicated that atypical antipsychotics (12) (sulpiride, metoclopramide, molindone, and Ro 22-1319) differ from classical neuroleptics (tricyclics, butyrophenones, butaclamol, diphenyl-piperidines) by lacking a lipophilic functional group on the basic nitrogen that could extend into the auxiliary binding site identified in our model. The absence of this lipophilic functionality may now be stated to be the characteristic which distinguishes selective D-2 dopamine receptor antagonists from non-selective antagonists. 

The purported mechanism of antipsychotic action of the butyrophenones and diphenyl-butylamines is believed to be as that of the phenothiazines, namely, at least in part, antagonism at postsynaptic DA receptors. It is not surprising that the spectrum of side effects is also similar, with extrapyramidal dystonic reactions at the top of the list. 

Aromatic ketones are often named by treating the benzene ring as a phenyl group, as in isopropyl phenyl ketone (Fig. 16.12). A few can be named through the lUPAC system in which the framework Ph—C=0 is indicated by the term ophenone and the remainder of the molecule designated by one of the alternative names in Rgure 16.12. Thus, diphenyl ketone is benzophenone, methyl phenyl ketone is acetophenone, ethyl phenyl ketone is propiophenone, and phenyl propyl ketone is butyrophenone (Fig. 16.12). 

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