Pyridine → HCID 131723706, compound

Participants

Reaction Steps

To pyridine (6 ml) at 0° C. was added portionwise lithium aluminium hydride (0.24 g). The mixture was allowed to warm to room temperature and was stirred for 24 h. Lithium iodide (0.220 g) and pyridine (1 ml) were added and the reaction stirred for a further 1 h. 5-Bromomethyl-2-chloro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (0.30 g, Example 8b) in dry pyridine (2 ml) was added to the solution at room temperature. After 2 h, the mixture was quenched at 0° C. with a cold 15% aqueous solution of acetic acid, stirred for an hour and concentrated under vacuum. The residue was taken in 1N sodium hydroxide, extracted with dichloromethane and the organic layers dried over magnesium sulfate. The crude material was purified on silicagel (2 to 10% 7N ammonia in methanol/dichloromethane) then treated with a 4N solution of hydrogen chloride in dioxane and methanol to give the title compound (0.20 g).

Provenance & Evidence