Diphenylacetic acid chloride

Oxyphenisatin acetate Diphenylacetic acid chloride Diphenpyramide Thiphenamil HCI Diphenyl acetone Diphenadione Diphenylacetonitrile Doxapram HCI Methadone HCI Diphenylacetyl chloride Piperidolate... 

Esters of diphenylacetic acids with derivatives of ethanol-amine show mainly the antispasmodic component of the atropine complex of biologic activities. As such they find use in treatment of the resolution of various spastic conditions such as, for example, gastrointestinal spasms. The prototype in this series, adiphenine (47), is obtained by treatment of diphenyl acetyl chloride with diethylaminoethanol. A somewhat more complex basic side chain is accessible by an interesting rearrangement. Reductive amination of furfural (42) results in reduction of the heterocyclic ring as well and formation of the aminomethyltetrahydro-furan (43). Treatment of this ether with hydrogen bromide in acetic acid leads to the hydroxypiperidine (45), possibly by the intermediacy of a carbonium ion such as 44. Acylation of the alcohol with diphenylacetyl chloride gives piperidolate (46). ... 

Diphenylacetic acid has been obtained by the reduction of benzilic acid with hydriodic acid and red phosphorus 1 by the treatment of phenylbromoacetic acid with benzene and zinc dust,2 or with benzene and aluminum chloride 3 by the hydrolysis of diphenylacetonitrile 4 by heating a-diphenyldichloroethyl-ene with alcoholic sodium ethylate 5 by heating benzilic acid 6 from diphenylmethane, mercury diethyl, sodium and carbon dioxide 7 by the oxidation of a,a,5,S-tetraphenyl- 8-butine 8 by the decomposition of some complex derivatives obtained from diphenylketene 9 by the hydrolysis of diphenyl-5,5-hydan-toin 10 by the treatment of diphenylbromoacetic acid with copper 11 by the oxidation of dichlorodiphenylcrotonic acid.12... 

Aryl-substituted glycolic acids have been successfully reduced in high yields by several procedures. Refluxing with phosphorus and iodine in glacial acetic acid is described for the preparations of diphenylacetic acid (97%), 4-fluorenecarboxylic acid (92%), ° and a series of a-naphthyl-alkylacetic acids and biphenylalkylacetic acids. In a slight variation of this procedure, a mixture of potassium iodide, phosphorus, and phosphoric acid is used. Stannous chloride in a mixture of hydrochloric, hydriodie, and acetic acids has been employed in the preparation of... 

Diperoxo-oxohexamethylphosphoramido-molybdenum(Vl), 203-204 Diphenoquinones, 270 Diphenyl, 377 Diphenylacetic acid, 301 Diphenylacetyl chloride, 527 Diphenylacetylene, 51, 117, 276-277, 432, 491... 

Decarbonylation. Sheehan and Frankenfeld treated a-imilino-a,a-diphenylacetic acid (1) with tosyl chloride in pyridine with the expectation of obtaining the N-tosyl derivative but instead characterized the products as benzophenone anil (3), carbon monoxide, and pyridinium tosylate. They postulate the intermediate formation of the mixed anhydride (2). 

Vorliinder showed that benzene plays no rule in the reaction (CS also can be used hut is less satisfactory) and noted that diphcnylchluroacetic acid is not an intermodiulc, since it reacts with benzene and aluminum chloride to give triphenyi-acetic acid. He noted also thal diphenylacetic acid does not react with aluminum chloride, that diphenylcurblnul gives products other than liuorene derivatives, and... 

The intermediate diphenylacetyl chloride can be prepared with a good yield by the acylation of diphenylacetic acid with thionyl chloride. 

Benzyl alcohol and benzene in a mixture of glacial acetic acid and sulfuric acid give diphenylmethane even at room temperature,646 and diphenyl-methanol gives an almost theoretical yield of diphenyl-p-tolylmethane when boiled with toluene and phosphoric oxide 647 diphenylacetic acid is formed in yields up to 96% on reaction of mandelic acid with benzene in the presence of aluminum chloride.648... 

To a solution of 0.56 gm (5.1 mole) of / -phenylenediamine and 1.0 gm (10.3 mole) of triethylamine in 1(K) ml of dry ether is added dropwise a solution of 2.37 gm (10.3 mole) of diphenylacetyl chloride in 20 ml of dry ether (diphenylacetylchloride is prepared from diphenylacetic acid and thionyl chloride) [25]. Fine, white crystals immediately appear and the reaction mixture is continuously stirred for 18 hr. The resulting solid is filtered, washed with cold water and dried to give, after recrystallization from DMF-water, 1.67 gm (66%), m.p. 333°-336°C. 

A novel formal decarboxylation of the amino acid a-anilino-a,a-diphenylacetic acid has been observed upon treatment with tosyl chloride in pyridine. It has been proposed that a mixed anhydride of p-toluenesulfonic acid has undergone an elimination viaiV-deprotonation and synchronous extrusion of carbon monoxide in this reaction. Interestingly, no A-tosylation occurs (eq 22). 

Dimethylaminoethyl methacrylate methyl chloride quat. diphenylacetic acid mfg. 

J ry pyridine added to a suspension of a-anilino-a,a-diphenylacetic acid and p-toluenesulfonyl chloride in dry benzene, and refluxed 7 hrs. benzo-phenone anil. Y 62.4%.—No reaction occurs with aq. NaOH in place of pyridine. J.G. Sheehan and J. W. Frankenfeld, J. Org. Ghem. 27, 628 (1962). 

The use of phenylpiperidinols rather than the meperidine-related piperidines as the basic component in antidiarrheal compounds results in retention of activity. The fact that the base is not directly related to a narcotic presumably leads to greater selectivity of action on the gut. Ring scission of butyrolactone 98 (obtainable by alkylation of a diphenylacetate ester with ethylene oxide) with hydrogen bromide gives the bromo acid 99. This is then converted to the dimethylamide by successive treatment with thionyl chloride and dimethylamine. 

Acyl radicals and acyl anions are proposed intermediates in the reduction of phenylacetyl chloride and hydrocinnamoyl chloride at mercury in MeCN [223]. Among the products obtained from the reduction of phenylacetyl chloride are 1,4-diphenyl-2-butene-2,3-diol diphenylacetate, phenylacetaldehyde, toluene, 1,3-diphenyl-acetone, and l,4-diphenyl-2,3-butanediol, as well as phenylacetic acid and phenylacetic acid anhydride. Analogous products arise from the reduction of hydrocinnamoyl chloride l,6-diphenyl-3-hexene-3,4-diol dihydrocinnamate, hydrocinnamaldehyde, ethyl benzene, l,6-diphenyl-3,4-hexanediol, hydrocinnamic acid, and hydrocinnamic acid anhydride. 

Adiphenine Hydrochloride, a-Phenylbenzeneace-tic acid 2 (diethyhmino)ethyl enter hydrochloride 2-diethyl-aminoethyl diphenylacetate hydrochloride diphenylacetyldi -ethylaminoethanol hydrochloride Trasentine hydrochloride Dipfiacif hydrochloride Spasmolytin Difacil hydrochloride Patrovina. C H CINO. mol wt 347,87. C 69.05% H 7.53%, Cl IQ.]9%, N 4.03%, O 9.20%. Antiniuscarinic anti-spasmodic. Prepd by the action of diphenylacetyl chloride or diphenyl ketene on diethylaminoethanol Swiss pat, 190,541 0937 to Ciba) Ger. par . 626,539 653,778 (1937), Crystal and molecular structure Guy, Hamor, J. Chant,... 

Tropacine. endo-a-Phenylbenzeneacetic acid ( methyt-8-azabicyclo[3.2,l]oct-3-yl ester laH.SaH-tropon-3a-ol diphenylacetate diphen ylacet ic acid 3c<-tropanyl ester 3a-tr0panyl diphenylacetate tropine diphenylacetate. C22-Hjjn02 mol wt 335.43. C 78.77%. H 7.51%, N 4.18%, O 9.54%. Prepd from tropine and diphenyiacetyl chloride Swiss pat. 202,181 (1939 to Ciba), C.A. 33, 8922 (1939) Friess et af., Toxicol. AppL PharmacoL 2, 574 (I960). 

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