Synthesis of 2-piperazinones and 1,4-diaza-2-keto-cycloheptanes

Details Synthesis of 2-piperazinones and 1,4-diaza-2-keto-cycloheptanes Synthesis of 2-piperazinones and 1,4-diaza-2-keto-cycloheptanes

1979-05-29

1980-12-23

Jiles, Henry R.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

544384, C07D24308, C07D24118

Patent

active

042409616

ABSTRACT:
Substituted 2-piperazinones are prepared by reacting a substituted 1,2-diamine with (a) an acyclic or cyclic cyanohydrin acetate, (b) a haloform, and (c) alkali metal hydroxide, in the presence of a suitable organic solvent, at ambient pressure and temperature preferably lower than about 20.degree. C. In an analogous manner, substituted 1,4-diaza-2-keto-cycloheptanes are prepared by reacting substituted 1,3-propane-diamines. In this synthesis, referred to as "the cyanohydrin acetate synthesis," the reaction is accelerated with a phase transfer catalyst selected from the group consisting of a polyether, an onium salt, and a tertiary amine. This synthesis yields predominantly a 2-keto-diazacycloalkane with substituents desirably substituted on carbon atoms on either side of the N.sup.4 atom of the diaza ring.

REFERENCES:
patent: 2649450 (1953-08-01), Strong et al.
patent: 2700668 (1955-01-01), Strong et al.
patent: 4167512 (1929-09-01), Lai

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