Benzene → HCID 21404764, compound

Participants

Reaction Steps

To 7.1 parts of N,N-dimethyl-N-(2-[5,6,7,8-tetrahydro-8-hydroxy-3-methoxyisoquinol-8-yl]prop-2-en-1-yl)amine in 31 parts of benzene and 34.5 parts of pyridine is added 4.5 parts of phosphorous oxychloride, dropwise and at room temperature. That solution is stirred at room temperature for several hours, then cooled in an ice bath. 25 Parts of water is added slowly followed by enough 5% aqueous sodium hydroxide solution to bring the pH of the solution to about 10. Ether is added and the organic and aqueous layers separated. The aqueous layer is extracted with ether and the extracts washed with saturated sodium chloride and dried over anhydrous sodium sulfate. Approximately 200 parts of n-hexane is added to the solution, followed by a portion of charcoal. That mixture is filtered through diatomaceous earth to give a light yellow solution which, upon solvent removal, affords a yellow oil yielding upon crystallization N,N-dimethyl-N-(2-[5,6-dihydro-3-methoxyisoquinol-8-yl]prop-2-en-1-yl)amine. A portion of that material is distilled and the distillate is taken up into methanol-water and upon standing yields crystals melting at about 42°-45° C.

Provenance & Evidence