GB664840A - Process for the manufacture of 1-aryl-cyclopentene-(3)-1-nitriles and basic esters and amides of 1-aryl-cyclopentene-(3)-1-carboxylic acids - Google Patents

Abstract

1 - Aryl - cyclopentene - (3) - 1 - nitriles are obtained by condensing arylacetonitriles with 1 : 4 - dihalogenbutene - 2; the aryl group may be phenyl substituted by methyl, methoxy, or halogen, indanyl or tetralyl; the nitriles are hydrolysed to carboxylic acids from which basic esters and amides of the general formula <FORM:0664840/IV (b)/1> in which R1 and R2 represent substituents as above, X is -O-, -NH-, -N(CH3)- or -N(C2H5)-, n is 2-6, and Am is a dialkyl-or dialkenylamino radical, the alkyl or alkenyl group of which contains 1-3 carbon atoms, as pyrrolidino-, piperidino- or morpholino-radical, are obtained by the reaction of their reactive functional derivatives such as halides, anhydrides and esters with suitable amino-alcohols, metal derivatives thereof, or with diamines. The same products are also obtained by reaction of the acids, their salts or metal amides with reactive esters of amino-alcohols, and by reaction of a reactive ester (such as halide or arylsulpho-) of the oxyalkyl ester or oxyalkyl amide of the acids with diamines containing the above mentioned groups Am; the amide N-atom may be alkylated if desired. The products may all be hydrogenated to the corresponding 1-aryl-cyclopentane derivatives. In examples, the preparations of the nitrile, the acid by hydrolysis, the b -diethylaminoethylester and amide hydrochlorides, are described in detail, and a list is given of, and tables give physical constants for, numerous derivatives substituted as described in the general formula. Specification 582,535 is referred to. 1 : 4 - dichlorobutene - 2 is obtained by the action of hydrochloric acid on butane-diol, and purifying.