Butyrophenone


Equip a 1500 ml. three-necked flask with an efficient mercury-sealed stirrer, a separatory funnel protected by a calcium chloride (or cotton wool) tube, and a double surface reflux condenser attached to a gas absorption device (Fig. 77, 8, 1, c). Weigh out 140 g. of finely-powdered, anhydrous aluminium chloride under sodium-dried A.R. benzene, and transfer the sohd to the flask already containing 231 g. (263 ml.) of anhydrous A.R. benzene. Place 105 g. (102 ml.) of n-butyryl chloride, b.p. 100-102° (Section 111,87) in the separatory funnel, run in 3-4 ml. into the flask and stir vigorously. Warm the flask gently to start the reaction (. c., until hydrogen chloride is evolved), remove the source of heat, and continue the addition during 2 hours. The reaction mixture darkens considerably. Reflux for 30 minutes to complete the reaction and allow to cool. Transfer the reaction mixture to a large separatory funnel and allow it to drip into about 2 litres of cold water in a 4-litre beaker, cooled externally in an ice bath, and vigorously agitated with an efficient mechanical stirrer. Separate the upper oily layer, wash it with 10 per cent, sodium hydroxide solution, then with water, and dry over anhydrous magnesium sulphate. Remove the benzene (Fig. 77, 75, 4, but use a 150 ml. Claisen flask), and distil the residue through an air condenser from an air bath. Collect the butyrophenone (a colourless liquid) at 227-230°. The yield is 75 g.  [c.732]

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.  [c.59]

Chloro-p-fluoro-butyrophenone Manufacturing Process  [c.1383]

Pharmacological Profiles of Antipsychotics. Most compounds used for antipsychotic therapy can be assigned to one of four stmcturaHy distinct groups. These are phenothiazines, eg, chlorpromazine (56) thioxanthenes, eg, chlorprothixene (57) diphenylbutylpiperidines, eg, pimozide (58) and butyrophenones, eg, haloperidol (59). Those antipsychotics most widely used clinically are included in Table 5. These compounds represent more than 97% of total units sold worldwide, but only about half of the antipsychotics clinically available. In view of the dopaminergic blocking action of compounds from these classes, some are used predorninantly or even solely as antiemetics, including alizapride [59338-93-1/, clebopride [55905-53-8] domperidone metoclopramide [364-62-5] oxypendyl [5585-93-3], and promethazine [60-87-7].  [c.235]

A dmg combination in popular use in dogs is a mixture of fentanyl [437-38-7], a narcotic analgesic, and droperidol [548-73-2], a butyrophenone tranquilizer. This combination produces a state of neuroleptanalgesia in which sedation and analgesia are achieved. The mixture is sold commercially and can be adrninistered by both subcutaneous and intramuscular injection. Because the combination contains a narcotic, it has the advantage of being rapidly reversible with narcotic antagonists such as naloxone [465-65-6] and nalorphine [62-67-9] once the effects are no longer needed.  [c.405]

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,  [c.306]

The cla.ssical antipsychotic agents, such as the phenothiazines and butyrophenones, owe much of their efficacy to their dopamine antagonist activity. A number of these agents find some utility as antiemetic compounds since emesis is also at least partly mediated by dopaminergic nerves. A dopamine antagonist from a quite different structural class seems to show some selectivity for those GI functions which involve dopamine receptors. The prototype, metoclopramide (140), has been found useful as an antiemetic compound as well as an agent for the control of the motility of the upper GI system. The finding that this drug controls emesis not effected by earlier dopamine antagonists, for example, that induced by chemotherapeutic agents used in canecr patients, has led to inereased interest in the benzamide elass.  [c.41]

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,  [c.1383]


See pages that mention the term Butyrophenone : [c.726]    [c.732]    [c.743]    [c.743]    [c.33]    [c.586]    [c.976]    [c.139]    [c.359]    [c.1121]    [c.306]    [c.49]   
See chapters in:

Textbook on organic chemistry  -> Butyrophenone


Textbook on organic chemistry (1974) -- [ c.726 , c.732 ]