[CH:1]1([C:4]2(O)[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3C=C(N3CCCCC3)[C:6]3[CH:21]=[CH:22][CH:23]=[CH:24][C:5]2=3)[CH2:3][CH2:2]1.[BrH:26].[C:27]([OH:30])(=O)[CH3:28]>C(#N)C>[Br:26][CH2:3][CH2:2][CH:1]=[C:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:28][C:27](=[O:30])[C:6]2[CH:21]=[CH:22][CH:23]=[CH:24][C:5]1=25-Cyclopropyl-10-piperidin-1-yl-5H-dibenzo[a,d]cyclohepten-5-ol (5) (69 mmol, 1.00 equiv.) was dissolved in 100 mL acetic acid, then 48% aqueous HBr (100 mL) was added and the resulting mixture was heated in a 100° C. oil bath. LC/MS analysis after 18 hours showed that the starting material was consumed. The mixture was diluted with H2O (100 mL) then extracted in a separatory funnel with ethyl ether (3×100 mL). The aqueous phase was discarded, after which the combined organic phases were washed with saturated sodium bicarbonate (3×50 mL). The aqueous phase was discarded, and the organic phase was filtered through a silica gel plug and concentrated under vacuum to obtain a thick brown oil, which was dissolved in acetonitrile (200 mL) and dried under vacuum. The residue was then dissolved in toluene (200 mL) and again dried under vacuum. The resulting crude 5-(3-bromo-propylidene)-5,11-dihydro-dibenzo[a,d]cyclohepten-10-one (6) was used without further purification in the next step. ESI MS m/z 327.0 (M+H)+. 1H NMR (d6-DMSO, 250 MHz): 7.98 (1H, d), 7.67-7.25 (7H, m), 5.76 (1H, t), 4.46 (1H, d), 3.73 (1H, d), 3.64 (2H, m), 2.83-2.50 (2H, m).
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