Butyrophenone

Propiophenone CgHjCOCHjCHj. Use 231 g. (263 ml.) of sodium-dried A. R. benzene, 140 g. of anhydrous aluminium chloride and 90 g. (84-5 ml.) of propionyl chloride (prepared from propionic acid compare Section 111,87). The yield of propiophenone, b.p. 214-217°, is 78 g. 

In a 1-litre three-necked flask, equipped as in Section IV,137, place 78-5 g. (52-5 ml.) of dry bromobenzene (Section IV,18), 200 ml. of dry 

These are all prepared in the same manner, viz., 0 5 mol of the derivative of the aromatic hydrocarbon, 150 g. of finely-powdered anhydrous aluminium chloride and 0 -5 mol of the acid anhydride. Thus — 

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When the cyclic component is benzene or naphthalene, the -ic acid or -oic acid of the acid corresponding to the acyl group is changed to -ophenone or -onaphthone, respectively. For example, C5H5—CO—CH2CH2CH3 can be named either butyrophenone (or butanophenone) or phenyl propyl ketone. 

Several methods are available to supplement the phenol alkylations described above. Primary alkylphenols can be produced using the more traditional Friedel-Crafts reaction. Thus an -butylphenol can be synthesized direcdy from a butyl haUde, phenol, and mild Lewis acid catalyst. Alternatively, butyryl chloride can be used to acylate phenol producing a butyrophenone. Reduction with hydrazine (a Wolff-Kishner reduction) generates butylphenol. 

The role of fluonne in the development of CNS agents has been reviewed [14] Ruonnated phenothiazines, typified by fluphenazine (7[Pg.1121]

The initial series of major tranquilizers consists of alkylated derivatives of 4-aryl-4-hydroxypiperidines. Construction of this ring system is accomplished by a set of rather unusual reactions. Condensation of methylstyrenes with formaldehyde and ammonium chloride afford the corresponding hexahydro-1,3-oxazines (119). Heating these oxazines in the presence of acid leads to rearrangement with loss of water to the tetrahydropyridines. Scheme 1 shows a possible reaction pathway for these transformations. Addition of hydrogen bromide affords the expected 4-bromo compound (121). This last is easily displaced by water to lead to the desired alcohol (122) The side chain (123) is obtained by Friedel-Crafts acylation of p-fluorobenzene with 4-chloro-butyryl chloride. Alkylation of the appropriate arylpiperidinol with 123 affords the desired butyrophenone derivative. Thus,... 

A mixture of 3.2 parts 4-chloro-p-fluoro-butyrophenone, 3.5 parts 1-oxo-4-phenyl-2,4,8-triazaspiro(4,5)decane, 2 parts Na COs hd 0.1 part Kl in 200 parts hexone is refluxed with stirring for 50 hours. The mixture is cooled to room temperature, 200 parts water are added and the layers are separated. The organic layer is dried over 10 parts MgSO, ... 

To distinguish between azobenzene and benzophenone, assuming reference spectra are not available for these compounds, it is a good idea to examine the mass spectra of aromatic ketones, such as acetophenone, butyrophenone, diphenyldiketone, and so forth. Complete identification is assured by obtaining or synthesizing the suspected component and analyzing it on the GC/MS system under the same GC conditions. If the retention time and the mass spectrum agree, then the identification is confirmed. 

Butyrophenones Butyrylcholinesterase C2 Domain C Kinase C-reactive Protein Ca2+-ATPase Ca2+-binding Proteins Ca2+ Channel Ca2+ Channel Antagonists Ca2+ Channel Blockers... 

But (i) Effect only antagonised by some neuroleptics, phenothiazines-YES thioxanthenes-YES butyrophenones-NO (metoclopromide inactive)... 

In 1952 reserpine, an alkaloid extract from the Indian snakewort plant, Rauwolfia serpentina, which had been used in that country to treat madness , was first tried in schizophrenia. The beneficial impact on patients and the hospital wards was dramatic, as was that a year later of chlorpromazine, a phenothiazine derivative and haloperidol, a butyrophenone. These latter two drugs and closely related derivatives remained the mainstay of therapy for almost 40 years. 

There is no shortage of these. The established ones belong to four main chemical groups (Fig. 17.1), the phenothiazines, thioxanthenes, butyrophenones and dibenzazepines. 

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