Reductive Alkylation of 2-Methylglutaronitrilewith Palladium Catalysts

DuPont Nylon Intermediates and Specialities, E. / . DuPont de Nemours & Co. Experimental Station, P. 0. Box 80302, Wilmington, Delaware 19880-0302 Abstract A study was made on the mono reductive alkylation of 2-methylglutaronitrile (MGN), a co-product in the synthesis of adiponitrile from butadiene and HCN, with dialkyl amines with the aim of understanding the chemistry and product selectivity associated with the use of Group VIII metals and Raney® catalysts for reductive alkylation of MGN to tertiary amines. This initiative was undertaken to fmd a selective catalyst for the synthesis of 5-diethylamino-2methylvaleronitrile (4), a known precursor to novoldiamine, which is used in the synthesis of the anti-malarial drug, chloroquine. The isomer, 2-diethylamino-2methylvaleronitrile (5) is also produced in the alkylation step.