Formaldehyde → HCID 54533758, compound

Participants

Reaction Steps

N-[2-[[(7-Methoxy-2-benzofuranyl)methyl]amino]ethyl]tricyclo[3.3.1.13,7 ]decane-1-carboxamide hydrochloride hemihydrate (1.0 g, 2.4 mmole), prepared as in Example 2, was dissolved in 100 ml of ethanol and 5 ml of 38% aqueous formaldehyde and 500 mg of 10% palladium on carbon were added. The mixture was hydrogenated at 50 psi on a Parr apparatus for 24 hours. The mixture was then filtered through celite and 300 ml of ether added. It was washed with 100 ml portions of saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride, dried over sodium sulfate, filtered and evaporated in vacuum. The residue was purified by column chromatography on 100 g of silica gel with chloroform as eluant and recrystallized from acetone/diethyl ether with the addition of 3 ml of 4N HCl/isopropanol to give 560 mg of the title compound as a white solid, monohydrochloride, quarter hydrate, m.p. 156°-158° C.

Provenance & Evidence