2.2.2. Synthesis of Compounds **3a**–**d**

To a solution of corresponding amines **1a**–**d** (1 mmol) in dichloromethane (30 mL), an equal amount of 2-(3-benzoylphenyl)propanoyl chloride **2** (1 mmol, 0.272 g) was added. After 10 min, triethylamine (1.2 mmol, 0.121 g) was added to the solution. After 30 min, the solution was washed with diluted hydrochloric acid, saturated solution of Na2CO3, and brine. The combined organic layers were dried over anhydrous Na2SO4, and the solvent was removed under reduced pressure. The new hybrid molecules were purified by filtration through short-column chromatography over neutral Al2O3.

**3a** *2-(3-benzoylphenyl)-1-(pyrrolidin-1-yl)propan-1-one*.

Light-yellow oil, Yield: 97% (0.299 g), Rf = 0.45 (diethyl ether), 1H NMR (400 MHz, CDCl3) δ 7.74–7.69 (m, 2H), 7.65 (t, *J* = 1.8 Hz, 1H), 7.57 (ddd, *J* = 7.6, 1.7, 1.2 Hz, 1H), 7.54–7.48 (m, 2H), 7.43–7.33 (m, 3H), 3.76 (q, *J* = 6.9 Hz, 1H), 3.50–3.38 (m, 2H), 3.38–3.11 (m, 2H), 1.87–1.76 (m, 2H), 1.75–1.69 (m, 2H), 1.42 (d, *J* = 6.9 Hz, 3H). 13C NMR (101 MHz, CDCl3) δ 196.63 (Ph-CO-Ph), 171.72 (C=O), 142.09 (Ar), 137.92 (Ar), 137.53 (Ar), 132.54 (Ar), 131.49 (Ar), 130.08 (Ar), 129.26 (Ar), 129.03 (Ar), 128.75 (Ar), 128.30 (Ar), 46.41 (CH2-N), 46.11 (CH2-N), 44.73 (CH), 26.10 (CH2), 24.17 (CH2), 20.12 (CH3). UV λmax, MeOH: 276 (*ε* = 15,270) nm. HRMS Electrospray ionization (ESI) *m*/*z* calcd for [M+H]+ C20H22NO2 <sup>+</sup> = 308.1645, found 308.1638 (mass error Δm = −2.27 ppm), calcd for [M+Na]+ C20H21NO2Na+ = 330.1465, found 330.1458 (mass error Δm = −2.12 ppm).

**3b** *2-(3-benzoylphenyl)-1-(piperidin-1-yl)propan-1-one.*

Light yellow oil, Yield: 94% (0.302 g), Rf = 0.85 (diethyl ether), 1H NMR (400 MHz, CDCl3) δ 7.73–7.69 (m, 2H), 7.62 (t, *J* = 1.8 Hz, 1H), 7.56 (dt, *J* = 7.6, 1.4 Hz, 1H), 7.54–7.49

(m, 1H), 7.46 (dt, *J* = 7.9, 1.5 Hz, 1H), 7.41 (dd, *J* = 8.2, 6.9 Hz, 2H), 7.36 (t, *J* = 7.6 Hz, 1H), 3.91 (q, *J* = 6.9 Hz, 1H), 3.50 (dddd, *J* = 105.8, 12.9, 6.5, 3.1 Hz, 2H), 3.27 (t, *J* = 5.5 Hz, 2H), 1.53–1.44 (m, 3H), 1.40 (d, *J* = 6.8 Hz, 3H), 1.33 (dtd, *J* = 17.1, 7.6, 4.6 Hz, 2H), 1.01 (dp, *J* = 12.1, 5.8 Hz, 1H). 13C NMR (101 MHz, CDCl3) δ 196.59 (Ph-CO-Ph), 171.26 (C=O), 142.74 (Ar), 138.08 (Ar), 137.54 (Ar), 132.54 (Ar), 131.23 (Ar), 130.05 (Ar), 128.96 (Ar), 128.79 (Ar), 128.59 (Ar), 128.31 (Ar), 46.65 (CH2-N), 43.19 (CH2-N), 42.82 (CH), 26.13 (CH2-CH2- CH2), 25.52 (CH2-CH2-CH2), 24.49 (CH2-CH2-CH2), 20.64 (CH3). UV λmax, MeOH: 276 (*ε* = 18,500) nm. HRMS Electrospray ionization (ESI) *m*/*z* calcd for [M+H]+ C21H24NO2 <sup>+</sup> = 322.1802, found 322.1795 (mass error Δm = −2.17 ppm), calcd for [M+Na]+ C21H23NO2Na+ = 344.1621, found 344.1614 (mass error Δm = −2.03 ppm).

**3c** *2-(3-benzoylphenyl)-1-(3,4-dihydroquinolin-1(2H)-yl)propan-1-one.*

Light-yellow oil, Yield: 95% (0.352 g), Rf = 0.48 (petroleum/diethyl ether = 1/1), 1H NMR (400 MHz, CDCl3) δ 7.70–7.62 (m, 2H), 7.57–7.47 (m, 2H), 7.43–7.31 (m, 4H), 7.28 (t, *J* = 7.5 Hz, 1H), 7.16–6.90 (m, 4H), 4.33–4.21 (m, 1H), 3.85 (s, 1H), 3.50 (dt, *J* = 13.0, 6.7 Hz, 1H), 2.54–2.41 (m, 1H), 2.23 (s, 1H), 1.81 (dp, *J* = 13.2, 6.6 Hz, 1H), 1.71 (s, 1H), 1.44 (d, *J* = 6.9 Hz, 3H). 13C NMR (101 MHz, CDCl3) δ 196.61 (Ph-CO-Ph), 171.52 (C=O), 142.17 (Ar), 137.87 (Ar), 137.66 (Ar), 132.59 (Ar), 131.42 (Ar), 130.15 (Ar), 129.34 (Ar), 128.68 (Ar), 128.57 (Ar), 128.42 (Ar), 126.30 (Ar), 125.09 (Ar), 42.90 (CH), 26.38 (CH2), 24.12 (CH2), 20.29 (CH3). UV λmax, MeOH: 273 (*ε* = 6940) nm. HRMS Electrospray ionization (ESI) *m*/*z* calcd for [M+H]+ C25H24NO2 <sup>+</sup> = 370.1802, found 370.1795 (mass error Δm = −1.89 ppm), calcd for [M+Na]<sup>+</sup> C25H23NO2Na+ = 392.1621, found 392.1613 (mass error Δm = −2.04 ppm). **3d** *2-(3-benzoylphenyl)-1-(3,4-dihydroisoquinolin-2(1H)-yl)propan-1-one.*

Light-yellow oil, Yield: 95% (0.350 g), Rf = 0.59 (diethyl ether), 1H NMR (400 MHz, CDCl3) δ 7.70–7.61 (m, 3H), 7.59–7.44 (m, 3H), 7.41–7.30 (m, 3H), 7.12–7.01 (m, 3H), 7.00–6.79 (m, 1H), 4.79–4.60 (m, 1H), 4.60–4.33 (m, 1H), 4.05–3.72 (m, 2H), 3.62–3.49 (m, 1H), 2.79–2.31 (m, 2H), 1.43 (dd, *J* = 6.9, 3.0 Hz, 3H). 13C NMR (101 MHz, CDCl3) δ 196.52 (Ph-CO-Ph), 172.09 (C=O), 142.32 (Ar), 138.17 (Ar), 137.43 (Ar), 133.92 (Ar), 133.41 (Ar), 132.58 (Ar), 131.27 (Ar), 131.25 (Ar), 130.04 (Ar), 129.00 (Ar), 128.90 (Ar), 128.77 (Ar), 128.31 (Ar), 126.69 (Ar), 126.55 (Ar), 126.28 (Ar), 47.39 (CH2), 44.70 (CH2), 43.39 (CH), 29.19 (CH2), 20.65 (CH3). UV λmax, MeOH: 235 (*ε* = 16,100) nm, 276 (*ε* = 10,400) nm. HRMS Electrospray ionization (ESI) *m*/*z* calcd for [M+H]+ C25H24NO2 <sup>+</sup> = 370.1802, found 370.1795 (mass error Δm = −1.89 ppm), calcd for [M+Na]<sup>+</sup> C25H23NO2Na+ = 392.1621, found 392.1613 (mass error Δm = −2.04 ppm).
