Hydrochloric Acid → HCID 12286596, compound

Participants

Reaction Steps

First of all, 1-(3-methoxyphenyl)-6-azabicyclo[3,2,1]-octane-7-one (VIII) is prepared by the six steps of (I) hydrolyzing 4-(3-methoxyphenyl)-4-cyano-1,1,-ethylenedioxy-cyclohexane (VII) with an alkali metal hydroxide(e.g., sodium hydroxide, potassium hydroxide) under heating in a solvent (e.g., methanol, ethanol, ethyleneglycol, a mixture of one of these solvents and water) to give 4-(3-methoxyphenyl)-4-carbamoyl-1,1-ethylenedioxy-cyclohexane, (2) reacting said carbamoyl-cyclohexane with an acid(e.g., hydrochloric acid, sulfuric acid, acetic acid) under heating, (3) brominating the resultant 4-(3-methoxyphenyl)-4-carbamoyl-cyclohexanone with bromine or pyridinium hydrobromide perbromide (C5H5N+HBr-) at room temperature in a solvent (e.g., acetic acid, tetrahydrofuran), (4) reacting the resultant 2-bromo-4-(3-methoxyphenyl)-4-carbamoyl-cyclohexanone with an alkali metal hydride (e.g., sodium hydride) or an alkali metal alkoxide (e.g., sodium methoxide, potassium methoxide, sodium ethoxide, potassium ethoxide) at room temperature in a solvent(e.g., methanol, ethanol, dimethoxyethane) to give 1-(3-methoxyphenyl)-6-azabicyclo[3,2,1]octane-4,7-dione, (5) refluxing a mixture of said product and hydrazine hydrate under heating in a solvent (e.g., ethanol, ethyleneglycol), and then (6) heating the resultant 1-(3-methoxyphenyl)-6-azabicyclo[3,2,1]octane-4,7-dione-4-hydrazone in the presence of an alkali agent(e.g., potassium hydroxide, potassium tert.-butoxide) in a solvent (e.g., toluene).

Provenance & Evidence