1-Methylpiperazine → 1-[(2E)-3-(4-{[3-Ethyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}phenyl)-2-propenoyl]-4-methylpiperazine

Participants

Reaction Steps

To a solution of (2E)-3-(4-{[3-Ethyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}phenyl)-2-propenoic acid (60) (0.10 g, 0.24 mmol) in CH2Cl2 (3 mL) at room temperature was added oxalyl chloride (63 μL, 0.71 mmol). The mixture was stirred at room temperature overnight. CH2Cl2 and excess of oxalyl chloride were removed under vacuum. The residue was dissolved in CH2Cl2 (4 mL), cooled in an ice bath, 1-methyl piperazine (40 μL, 0.35 mmol) was added. The resulting mixture was allowed to stir at room temperature overnight. Diluted with CH2Cl2 (50 mL), the mixture was washed with saturated aqueous NaHCO3, 0.5 N NaOH and brine, dried over Na2SO4, filtered, and the filtrate was concentrated to give the crude product as a yellow oil. The crude product was purified by flash chromatography over SiO2 with CHCl3:MeOH (75:1 to 50:1) to give 84 mg (70%) of compound 62 as a white foam. 1H NMR (400 MHz, CH3OH-d4): δ 1.09 (t, J=7.5 Hz, 3H), 2.32 (s, 3H), 2.47 (br s, 4H), 2.58 (q, J=7.5 Hz, 2H), 3.71 (br s, 4H), 3.92 (s, 3H), 6.54 (d, J=8.7 Hz, 2H), 6.91 (d, J=15.4 Hz, 1H), 7.02 (dd, J1=9.2 Hz, J2=2.4 Hz, 1H), 7.10-7.16 (m, 2H), 7.18-7.28 (m, 3H), 7.30 (d, J=2.4 Hz, 1H), 7.37 (d, J=8.8 Hz, 2H), 7.44 (d, J=15.4 Hz, 1H), 7.63 (d, J=9.3 Hz, 1H), 7.66 (s, 1H). LCMS (APCI): m/z 507 (M+H)+.

Provenance & Evidence