Diethylaminoethyl / -aminobenzoate

Diethyl ethylthioethyl phosphorothioate, 512 Diethyl isopropylmethylpyrimidinyl phosphorothioate, 528 Diethyl nitrophenyl phosphorothioate, 853 Diethyl oxide, 595 Diethyl phthalate, 538 Diethylamide nicotinic acid, 813 Diethylamine, 567 Diethylaminoacetoxylidide, 705 Diethylaminoethanol, 452, 805, 925 Diethylaminoethoxydimethylaminobenzothiazole, 525 Diethylaminoethoxyethyl ethylphenylbutyrate, 837 Diethylaminoethoxyethyl phenylcyclopentanecarboxylate, 431 Diethylaminoethyl aminobenzoate, 925 Diethylaminoethyl aminobutoxybenzoate, 840 Diethylaminoethyl aminochlorobenzoate, 451 Diethylaminoethyl 3-amino-4-propoxybenzoate, 943 Diethylaminoethyl 4-amino-2- propoxybenzoate, 936 Diethylaminoethyl benzilate, 375 Diethylaminoethyl bicyclohexylcarboxylate, 535 Diethylaminoethyl diphenylacetate, 320... 

Ir. the second step, the diethylaminoethyl 2-chloro-4-aminobenzoate hydrochloride is prepared by refluxing equimolar proportions of the hydrochloride of (3-diethylaminoethanol in a suitable inert solvent such as a mixture of dry toluene and tetrachloroethane and the hydrochloride of 2-chloro-4-aminobenzoyl chloride until the reaction as indicated by the cessation of hydrogen chloride evolution is complete. The supernatant solvents are decanted from the reaction product which can be conveniently purified by crystallization from absolute ethanol. 

An alternative purification can be effected by dissolving the reaction product in water. The ester base is liberated by rendering the clarified aqueous solution alkaline. Removal of the base from the alkaline solution is achieved by extraction with a Suitable solvent such as benzene or ether. The pure hydrochloride of diethylaminoethyl 2-chloro-4-aminobenzoate Is then precipitated from the dried extract by the addition of dry hydrogen chloride. After removal by filtration and recrystallization from ethanol it is found to have a melting point of 173° to 174°C. 

Procaine Procaine, the 2-diethylaminoethyl ester of 4-aminobenzoic acid (2.1.1), better known as novocaine, is synthesized in two ways. The first way consists of the direct reaction of the 4-aminobenzoic acid ethyl ester with 2-diethylaminoethanol in the presence of sodium ethoxide. The second way of synthesis is by reacting 4-nitrobenzoic acid with thionyl chloride, which gives the acid chloride (2.1.2), which is then esterified with iV,Ar-diethylaminoethanol. Subsequent reduction of the nitro group by hydrogenation of the resulting ester (2.1.3) into an amino group takes place in the presence of Raney nickel [ 1 ]. 

Chloroprocaine Chloroprocaine, the 2-diethylaminoethyl ester of 2-chloro-4-aminoben-zoic acid (2.1.5), is the ortho-chlorinated (in relation to the carbonyl group of the benzene ring) analog of procaine. Synthesis of this drag is accomplished by directly reacting the hydrochloride of the 4-amino-2-chlorbenzoic acid chloride (2.1.4) with hydrochloride of diethylaminoethanol. The hydrochloride of 4-amino-2-chlorbenzoic acid chloride needed for synthesis is synthesized by reacting 2-chloro -aminobenzoic acid with thionyl chloride [5],... 

Tetracaine Tetracaine, the 2-diethylaminoethyl ester of 4-butylaminobenzoic acid (2.1.6), is also structurally analogous to procaine, in which the amino group of the benzene ring is replaced by a butylamine radical. The methods for its synthesis are the same as the above-mentioned methods for procaine or chloroprocaine, with the exception of using 4-butylaminobenzoic acid in place of 4-aminobenzoic acid. There is also a proposed method of synthesis that comes directly from procaine (2.1.1). It consists on its direct reaction with butyric aldehyde and simultaneous reduction by hydrogen using a palladium on carbon catalyst [6]. 

Procaine hydrochloride (Novocain, 2-diethylaminoethyl-4-aminobenzoate) [51-05-8] M 272.8, m 153-156 , 154-156 , 156 . Recrystd from aqueous EtOH. It has solubility at 25 in H2O (86.3%), EtOH (2.6%) and Me2CO (1%), it is slightly soluble in CHCI3 but is almost insoluble in Et2O. The anhydrous free base is recrystd from ligroin or Et2O and has m 61 . [Einhorn A 371 125 1909 IR Szymanski and Panzica J Amer Pharm Assoc 47 443 7955]. 

Diethylamine-ethyl-p-aminobenzoate o-Octyloxybenzoyl chloride 2-Diethylaminoethyl chloride... 

Diethylaminoethyl p-aminobenzoate)] (aryl ester, tertiary amine) [Ruthenium red (= Synthetic RY-R [microscopy dye]... 

Towards the end of the 19th century, the German dye industry embarked on diversification based on its coal-tar intermediates. These became important medicinal products, including Bayer s aspirin, made from the intermediate salicylic acid (o-hydroxybenzoic acid). The first local anesthetics were esters of aminobenzoic acid. In 1906, Hoechst introduced the anesthetic novocaine (45), marketed as the hydrochloride of diethylaminoethyl p-aminobenzoate, based on the research of Alfred Einhom. Novocaine was the standard... 

Local anesthetics make use of the lipophobic property of an aromatic amine moiety, or its acyl derivative, that links with a hydrophilic amino acid. The products include the anilide lidocaine, or 2-(diethylamino)-A-(2,6-dimethylphenyl)acetamide (153), the toluidine derivative prilocaine and the century-old procaine, 2-diethylaminoethyl 4-aminobenzoate (154)84. The ester is prepared by reacting p-aminobenzoic acid with ethylene chlorohydrin and diethylamine. 

Metabutoxycaine Hydrochloride. 3-Amino-2-butoxybenzoic acid 2-diethylaminwlkyl ester hydrochloride 2-butoxy-3-aminobenzoic acid d-diethylaminoethyl ester hydrochloride p-diethylaminoethyl 2-butoxy-3-aminoben -zoate hydrochloride Primacaine hydrochloride. C H CI -N2Oy mol wt 344.88. C 59.20%, H 8.48%, Cl 10.28%, N 8.12%, O 13.92%. Prepn Brit, pat. 728,527 (1955 to Novo-col Chem.), GA 50, 5750 0956). I... 

Aminobenzoic acid 2-(diethylamino) ethyl ester p-Aminobenzoic acid diethylaminoethyl ester p-Aminobenzoic acid-2-diethylaminoethyl ester. See Procaine 4-Aminobenzoic acid 2-(diethylamino) ethyl ester hydrochloride p-Aminobenzoic acid-2-diethylaminoethyl ester, hydrochloride. See Procaine hydrochloride 4-Aminobenzoic acid ethyl ester. See Ethyl-p-aminobenzoate... 

Diethylaminoethanol p-Diethylaminoethanol N-Diethylaminoethanol N,N-Diethyl-2-aminoethanol. See Diethylaminoethanol Diethylaminoethanol-4-aminobenzoate hydrochloride. See Procaine hydrochloride Diethylaminoethyl acrylate CAS 2426-54-2... 

P-Diethylaminoethyl alcohol. See Diethylaminoethanol 2-Diethyl ami noethyl p-ami nobenzoate 4-(Diethylamino) ethyl 4-ami nobenzoate p-Diethylaminoethyl-4-aminobenzoate Diethylaminoethyl-p-aminobenzoate. See Procaine... 

Diethylamino) ethyl 4-aminobenzoate hydrochloride 2-Diethylaminoethyl-p-amlnobnzoate hydrochloride. See Procaine hydrochloride Diethylaminoethyl cellulose CAS 9013-34-7... 

Benzoic acid, p-amino-, 2-(diethylamino) ethyl ester, monohydrochloride Diethylaminoethanol-4-aminobenzoate hydrochloride 2-(Diethylamino) ethyl 4-aminobenzoate hydrochloride 2-Diethylaminoethyl-p-aminobnzoate hydrochloride Ethyl-p-aminobenzoate hydrochloride Empirical C13H20N2O2 CIH Properties Wh. cryst. powd., odorless, tasteless sol. in dil. acids less sol. in chloroform, ether, alcohol very si. sol. in water m.w. 272.81 m.p. 88-92 C... 

The property of producing local anaesthesia is also shown by other products than alkamine esters, e.g., benzyl alcohol and its homologues, saligenin, and the esters of aminoaromatic acids j such as the ethyl and diethylaminoethyl esters of 4-aminobenzoic acid. 

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