Benzene → (Z)-2-cyclohexanecarbonyl-1,2,3,4-tetrahydro-6,7-dimethoxy-1-[(3,4,5-trimethoxyphenyl)methylene]isoquinoline

Participants

Reaction Steps

To a suspension of 5 parts of 3,4-dihydro-6,7-dimethoxy-1-[(3,4,5-trimethoxyphenyl)methylene]isoquinoline in 50 parts of benzene is added 15 parts of pyridine, followed by 3 parts of cyclohexanecarbonyl chloride. The resultant mixture is heated at the boiling point under reflux in a nitrogen atmosphere for 2 hours, then cooled, consecutively washed with water and aqueous 5% sodium becarbonate, dried over anhydrous sodium sulfate, and stripped of solvent by vacuum distillation. The residue is crystallized from a mixture of ethyl acetate and ether to afford (Z)-2-cyclohexanecarbonyl-1,2,3,4-tetrahydro-6,7-dimethoxy-1-[(3,4,5-trimethoxyphenyl)methylene]isoquinoline melting at 162°-164°.

Provenance & Evidence