1-Pyrrolidinamine → Aminopyrrolizine

Participants

Reaction Steps

A reactor was charged with 0.0675 g of 5% palladium/carbon and 3.9 g of methanol, hydrogen substitution was carried out, and the catalyst was activated. Then, 2.8 g of a tetrahydropyridazine methanol solution [composition: tetrahydropyridazine 23.77% by weight, 0.67 g (0.008 mole), pyrrolidine 1.61% by weight, 0.05 g (0.0006 mole), 1-aminopyrrolidine 1.36% by weight, 0.04 g (0.0004 mole)] was added to adjust it to a 10% by weight methanol solution of tetrahydropyridazine. Thereafter, at room temperature, a catalytic hydrogenation reaction was carried out under a normal pressure for 5 days. After the reaction, the reaction solution was analyzed by GC. The results were as follows: Hexahydropyridazine 46.98%, tetrahydropyridazine 22.84%, 1-aminopyrrolidine 23.89%, and pyrrolidine 3.91%, and the formation of hexahydropyridazine as the intended product was confirmed. The reaction selectivity was hexahydropyridazine 60.89%, 1-aminopyrrolidine 30.96%, and the conversion of tetrahydropyridazine was 77.16%. Incidentally, 1-aminopyrrolizine was formed from tetrahydropyridazine by a reduction side reaction, and the formation of pyrrolidine as a decomposition product was recognized.

Provenance & Evidence