Methanol → HCID 10223864, compound

Participants

Reaction Steps

To a stirred solution of N-(1-adamantylmethyl)-2-chloro-5-(3-oxopropyl)nicotinamide (Example 3(ii)) (0.10 g) in methanol (3 ml) and acetic acid (0.1 ml) was added. 3-aminopropanol (0.042 g) and the resulting solution was stirred for 2 hours and then sodium cyanoborohydride (0.020 g) was added and the reaction mixture stirred for 20 hours. The mixture was concentrated and the residue partitioned between 2M aqueous hydrochloric acid solution and ethyl acetate (2×10 ml). The layers were separated and the organic phase re-extracted with 2M aqueous hydrochloric acid solution (2×10 ml). The combined aqueous extracts were basified with 5M aqueous ammonium hydroxide solution, extracted into ethyl acetate (2×25 ml) and the combined extracts were dried over anhydrous magnesium sulfate, filtered and concentrated to afford the titled compound (0.075 g) as a white solid.

Provenance & Evidence