GB647846A - Improvements in or relating to basic alkyl esters and the preparation thereof - Google Patents

Abstract

Basic alkyl esters, of the general formula <FORM:0647846/IV (b)/1> (wherein R is hydrogen or a hydrocarbon radical, e.g. lower alkyl, aryl, cycloalkyl, aralkyl or alkenyl, R1 is a -naphthyl, n is 2, 3 or 4, and Y is -CH2-, -O-, -NH- or -S-), and salts thereof, are manufactured by reacting a -naphthylacetic acid or a hydrocarbon derivative thereof in which the hydrocarbon radical is attached to the a -aliphatic carbon atom, with a substituted alkyl halide of the general formula <FORM:0647846/IV (b)/2> to produce the hydrohalide of the ester, and, if desired, treating this with alkali to produce the free ester; or by treating an acid of the said kind with thionyl chloride, reacting the resulting acid chloride with excess of a substituted alkanol containing a piperidino, morpholino, piperazino or thiomorpholino group to produce the free ester, and, if desired, treating this with an acid (e.g. a hydrogen halide, acetic acid, tartaric acid, citric acid, sulphuric acid or methylsulphuric acid) or an acid anhydride to convert it into a salt. The reaction in either case is preferably effected in the presence of a low-boiling organic solvent, e.g. isopropyl or butyl alcohol or benzene. The products are useful as antispasmodics or as intermediates in the preparation of complex organic derivatives. Specified starting materials are, on the one hand, a - naphthylacetic acid, a - (a 1 - naphthyl) - phenyl- and -cyclohexyl-acetic acid, a -(a 1-naphthyl) - phenylpropionic acid, and a - (a 1 - naphthyl)-propionic, -n-butyric, -n-pentanoic, -n-hexanoic and -D 4-n-hexenoic acids, and, on the other hand, b -morpholino- and b -piperidinoethyl chloride, g -piperidinopropyl bromide, d -morpholino-n-butyl bromide, b -piperazinoethyl iodide, g -thiomorpholinopropyl chloride, d - thiomorpholino - n - butyl chloride, b - piperidinoethanol and b -morpholinoethanol. Examples describe the use of certain of these starting materials, and a list of additional products is given. a -(a 1-Naphthyl)-n-butyric, -n-pentanoic and -n-hexanoic acids are obtainable by treating diethyl-a -naphthylmalonate with sodium in benzene and then with ethyl, propyl or butyl iodide, and saponifying and decarboxylating the resulting diethyl alkyl-a -naphthylmalonates. The Specification as open to inspection under Sect. 91 comprises also the manufacture of esters of the general formula above in which R1 represents p-xenyl. Additional starting materials specified are p-xenylacetic acid, a -(p-xenyl)-phenyl- and -cyclohexyl-acetic acid, a -(p-xenyl)-phenylpropionic acid, and a -(p-xenyl)-propionic, -n-butyric, -n-pentanoic, -n-hexanoic and - 4-n-hexanoic acids. This subject-matter does not appear in the Specification as accepted.