Pyrrolidone, from succinimide

Over nickel catalysts, phthalimide (eq. 10.48),80 and IV-substituted succinimides and glutarimides are hydrogenated to give the lactams at 200-220°C.77 Hydrogenations were rather slow at these temperatures, but use of dioxane for Raney Ni at temperatures above 220°C should be avoided.81 The reaction with /V-pcntylsuccinimide (eq. 10.49) was incomplete even after two applications of catalyst. The low yield of the pyrrolidone probably resulted from the difficulty of separating the pyrrolidone from the imide. 

L-Theanine is the most abundant amino acid in tea flush. Volatiles produced by pyrolysis at 180°C of (A) L-theanine, (B) (-)-epigallocatechin gallate and (C) a mixture of (A) and (B) were examined. The procedure was the same as that reported earlier for the pyrolysis of 8-carotene. The results of the GC-MS analysis are shown in Figure 4. From L-theanine alone, a large amount of N-ethyl-formamide was formed, along with ethyl amine, propyl amine, 2-pyrrolidone, N-ethyl-succinimide and l-ethyl-3,4-dehydro-pyrrol idone. 

Oxidations with peroxybenzoic acid are carried out in solutions in dichloromethane, chloroform, benzene, ether, or ethyl acetate at or below room temperature and include epoxidation of double bonds [295, 296, 297, 298, 299, 300, 301], oxidation of benzaldehydes to carboxylic acids or phenols [302], the Baeyer-Villiger reaction of ketones [303, 304, 305, 306, 307], and oxidation of sulfides to sulfoxides [308, 309]. Peroxybenzoic acid is also used for the anti hydroxylation of double bonds [310], the oxidation of pyrrolidines to pyrrolidones [377] and of pyrroles to succinimides [377], and the preparation of azoxy compounds from azo compounds [372]. 

Aminobutyric acid has been prepared by the electrolytic reduction of succinimide to pyrrolidone and hydrolysis of the latter by means of barium hydroxide,1 by the oxidation of piperylurethan with fuming nitric acid and the treatment of the resulting product with concentrated hydrochloric acid in sealed tubes at 100°,3 and by the hydrolysis of the condensation product from 2V-(/3-bromoethyl)-phthalimide and sodiomalonic ester.4 The present method is a slight modification of that of Gabriel.2... 

Insertion of an extra methylene group between the succinimide or pyrrolidone moiety and the butynyl chain (R = (CH2)2 in formulae 29-33) retains the separation of effects but the central potency is substantially less than that of atropine [421-423], Promising results have been reported in initial clinical trials fora compound from this series, l-[4-(2-oxopyrrolidino)but-2-ynyl]-2, 3,4,5,6,7-hexahydroazepine (34) [424], and many congeners of this particular agent would seem worthy of further clinical study in Parkinsonism. 

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