8-Methoxy-2,3,4,5,6,7-hexahydroazocine → HCID 11771845, compound

Participants

Reaction Conditions

Reaction Steps

To 0.700 mL of the 0.3 M solution of 4-pentylbicyclo[2.2.2]octane-1-carbohydrazide in DMF (crude, prepared as in step A above) was added 8-methoxy-2,3,4,5,6,7-hexahydroazocine (29.6 mg, 1 eq) and the reaction was heated to 130° C. overnight. After this time the solvent was removed under reduced pressure and the residue was chromatographed on C-18 reverse phase (gradient 90% water to 100% acetonitrile, 0.1% TFA). The fractions containing the compound were determined by LCMS, added to 200 mL of methylene chloride, and extracted with saturated sodium bicarbonate. The organic layer was dried over magnesium sulfate and evaporated under diminished pressure. The residue was lyophilized from benzene to afford 3-(4-pentylbicyclo[2.2.2]oct-1-yl)-5,6,7,8,9,10-hexahydro[1,2,4]triazolo[4,3-a]azocine (1-C); MS (ESI+)=300.3 (M+1)

Provenance & Evidence