92-12-6 Usage
Originator
Bristalin, Bristol ,US,1952
Manufacturing Process
Sodium methylate is made by dropping 11.7 g of sodium strips into 199 ml of absolute methanol in a 1-liter three-necked flask. 93.9 g of o-benzylphenol are dissolved in 200 ml of dry toluene and added to the sodium methylate solution. The solution is distilled until the boiling point of toluene is reached. At the end of the distillation, enough toluene is added to restore the original volume of solvent.109.5 g of dimethylaminoethyl chloride hydrochloride and 200 ml of toluene are placed in a 1-liter Erlenmeyer flask, cooled in an ice bath, and decomposed with 167.5 g of 20% sodium hydroxide solution. The toluene and water layers are separated, and the water layer is extracted again with 50 ml of toluene. The toluene layers are combined, washed with saturated salt solution, and dried over anhydrous potassium carbonate.The dried dimethylaminoethyl chloride solution is poured into the toluene solution of the sodium salt of o-benzylphenol, heated to reflux, and refluxed 16 hours. After refluxing, enough water is added to the mixture to dissolve the precipitated solid. The layers are separated, and the toluene layer is further washed with water until the water extract is just slightly alkaline. The toluene solution is then made acid with 6N hydrochloric acid and extracted with water until no cloudiness is produced when the extract is made alkaline. The acidic aqueous extract is washed with ether, then made alkaline with 20% sodium hydroxide solution, and extracted into ether. The ether solution is washed several times with water, then with saturated salt solution, and is dried over anhydrous potassium carbonate. The dried solution is filtered and distilled. The product distills at 143.5°C/1 mm; 69.7 g of pale yellow oil are recovered.57.1 g of the free base are dissolved in ether and precipitated with dry HCl. 66.0 g of crude hydrochloride are recovered. The hydrochloride is dissolved in 130 ml of reagent acetone by boiling, filtered hot, and allowed to cool. The crystalline material obtained on cooling is filtered, washed with a little acetone, washed with ether, and dried in vacuo. 44.8 g, MP 119.5°C to 121°C, are recovered from the first crop of crystals. Ethyl acetate may also be used as the solvent for recrystallization.
Therapeutic Function
Antihistaminic
Check Digit Verification of cas no
The CAS Registry Mumber 92-12-6 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 2 respectively; the second part has 2 digits, 1 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 92-12:
(4*9)+(3*2)+(2*1)+(1*2)=46
46 % 10 = 6
So 92-12-6 is a valid CAS Registry Number.
InChI:InChI=1/C17H21NO/c1-18(2)12-13-19-17-11-7-6-10-16(17)14-15-8-4-3-5-9-15/h3-11H,12-14H2,1-2H3
92-12-6Relevant articles and documents
Mustard Carbonate Analogues as Sustainable Reagents for the Aminoalkylation of Phenols
Annatelli, Mattia,Trapasso, Giacomo,Salaris, Claudio,Salata, Cristiano,Castellano, Sabrina,Aricò, Fabio
supporting information, p. 3459 - 3464 (2021/05/24)
N,N-dialkyl ethylamine moiety can be found in numerous scaffolds of macromolecules, catalysts, and especially pharmaceuticals. Common synthetic procedures for its incorporation in a substrate relies on the use of a nitrogen mustard gas or on multistep syntheses featuring chlorine hazardous/toxic chemistry. Reported herein is a one-pot synthetic approach for the easy introduction of aminoalkyl chain into different phenolic substrates through dialkyl carbonate (β-aminocarbonate) chemistry. This new direct alcohol substitution avoids the use of chlorine chemistry, and it is efficient on numerous pharmacophore scaffolds with good to quantitative yield. The cytotoxicity via MTT of the β-aminocarbonate, key intermediate of this synthetic approach, was also evaluated and compared with its alcohol precursor.
Synthesis and antidepressant activity of substituted (ω-Aminoalkoxy)benzene derivatives
Kikumoto,Tobe,Tonomura
, p. 145 - 148 (2007/10/02)
A series of substituted (ω-aminoalkoxy)benzene derivatives has been synthesized and screened for potential antidepressant activities. The effect of structural variation of these molecules has been systematically examined. Antidepressant activity was clearly displayed by 2-benzyl-1-[4-(methylamino)butoxy]benzene (7), 2-(2-hydroxybenzyl)-1-[4(methylamino)butoxy]benzene (19), 1-[4-(methylamino)butoxy]-2-phenoxybenzene (29), and 1-[4-(methylamino)butoxy]-2-(phenylthio)benzene (31) in further pharmacological studies. These compounds did not possess the anticholinergic, antihistaminic, and muscle-relaxant side effects common to tricyclic antidepressants.
