The 3-and 4benzoylpiperidines and 3-benzoylpyrrolidines were prepared by the reaction of l-acetylisonipecotoyl or 1-acetylnipecotoyl chloride with a substituted aromatic compound under Friedel-Crafts conditions or by treatment of the cyanopiperidines and pyrrolidines with an arylmagnesium halide. Alkylation gave the I-substituted compounds which were evaluated as CNS depressants. The I-substituted 4(p-fluorobenzoyl)piperidines were the most active compounds, several of which were more potent than chlorpromazine, triperidol, or haloperidol in the fighting mouse assay.

The pyrrolidine nucleus has been incorporated into many anticholinergic drugs as the basic moiety of the dialkylaminoalkyl substituted-phenylacetate type. These compounds can be divided into two main structural categories-those in which pyrrolidine serves as the terminal basic group of the alkyl chain (I); and those in which the nucleus itself is part of the aminoalkyl chain (II).1-4

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passed through the reaction mixture and then through 3% hydrochloric acid for 15 hours. The acid solution was evaporated to dryness in DQCUO and the white, crystalline residue identified as a mixture of methylamine hydrochloride, m.p. 225O, and ammonium chloride, no m.p. t o 300°, by recrystallization from methanol-ether and by vapor phase chromatography. For the latter a Perkin-Elmer model 154 Vapor Fractometer with a 1-m. triethanolamine impregnated Celite column wasused a t 79". The mixture of amines was introduced in methanol solution after liberation from their hydrochlorides by addition of methanolic potassium hydroxide.Four sharp maxima were obtained corresponding to control peaks obtained for ammonia, methylamine, methanol and water. The area under the ammonia peak was smaller than that from methylamine. Control Experiments.-(a)The above procedure was repeated with 1 g. (0.0032 mole) of 4-ami110-6-cliloro-N,X'dimethyl-nt-benzenedisulfonainide (Yh). Onlv a sm,lll amount of ammonium chloride WAS isolated in this case. S o trace of methylamine could be detected by vapor phase chromatography.A suspension of 0.50 g. (0.0016 mole' of X wds refluxed for 2 hours in 60 ml. of 10yc hydrochloric acid, cooled and made strongly basic with saturated sodium hydroxide solution. A stream of nitrogen T V~T passed through the solution and through a trap of 3y0 hydrochloric acid for 15 hours Evaporation of the acid to tiryneqs did not le tve any residue.SUMMIT, N. J. (b) [CONTRIBUTION FROM THE CHEMICAL RESEARCH LABORATORY, A. H. ROBISS Co., INC.] When (a) 3-(o-methoxyphenoxy)-1,2-propanediol (11) is fused at 180-200O with two molar equivalents of urea or when (b) 2-hydroxy-3-(o-methoxyphenoxy)-propyl carbamate (I) and one molar equivalent of urea are similarly fused, the major product is 5-(o-methoxyphenoxymethyl)-2-oxazolidinone (IIIa). A sequence of reactions by which the oxazolidinone ring is formed under these conditions has been investigated and these reactions are discussed. Following method (a) twentyfive 5-aryloxymethyl-2-oxazolidinones, in which the substitution in the aryl nucleus is alkyl, alkyloxy and/or halogen, have been prepared for pharmacological testing. A total of nineteen corresponding N-substituted-5-aryloxymethyl-2-oxazolidinones, prepared by condensation of l-amin0-3-aryloxy-2-prop~1101~ with ethyl carbonate or phosgene, are also reported.In an effort to develop other processes of preparing the skeletal muscle relaxant 2-hydroxy-3-(o-methoxyphenoxy)-propyl carbamate (I) the reaction between 3-(0-methoxyphenoxy) -1,2-propanediol (11) and urea was studied. Instead of yielding the desired carbamate, the fusion of these 0 J-FHd I1 i OCHi CHCH? OCKH, \= I

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