3-Pyridinemethanamine → HCID 131724642, compound

Participants

Reaction Steps

To a mixed anhydride solution prepared from 4.0 g (8.2 mmol) of borrelidin according to Example 34.2 ml (41.2 mmol, 4.46 g) of 3-picolylamine were added. After stirring for 3 hours, the starting borrelidin (Rf=0.43) disappeared and the product (Rf=0.24) appeared, which was proved by thin-layer chromatography (silica gel plate, eluent system: chloroform/methanol 95:5). The reaction mixture was evaporated to dryness. The dry residue was dissolved in 500 ml of chloroform, washed with 3×1500 ml of water, dried over sodium sulfate and evaporated to dryness. The dry residue was chromatographed on a silica gel column with mixtures of chloroform and ethyl acetate of increasing ethyl acetate content. The fractions containing the product eluting with a 2:8 eluting mixture were combined and evaporated to dryness. To the thus-obtained solidifying oily substance (3.62 g) 4 ml of ethyl acetate and 20 ml of n-hexane were added, the solid material was triturated and then filtered. In this way 3.04 g product were obtained. Mp.: 99-105° C.

Provenance & Evidence