[C:1](Cl)(=[O:10])/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br.[Cl:13][C:14]1[C:23]([OH:24])=[C:22]([OH:25])[C:21]([Cl:26])=[C:20]2[C:15]=1[CH2:16][CH2:17][NH:18][CH2:19]2.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C>[Cl:13][C:14]1[C:23]([OH:24])=[C:22]([OH:25])[C:21]([Cl:26])=[C:20]2[C:15]=1[CH2:16][CH2:17][N:18]([C:1](=[O:10])/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH2:19]2
trans-Cinnamoyl chloride (79 mg, 0.476 mmol) was suspended in DMF (7 mL) together with 5,8-dichloro-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrobromide (150 mg, 0.476 mmol) followed by triethylamine (133 μL, 0.952 mmol). The resulting mixture was stirred at room temperature for 16 hours and then diluted with ethyl acetate (50 mL). The resulting mixture was washed twice with saturated sodium bicarbonate (2×40 mL), dried (MgSO4) and evaporated into a yellowish mass. Purification with column chromatography (petroleum ether/ethyl acetate 1/1→1/2) yielded 69 mg (40%) of the title compound as a yellowish solid.
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