Cesium carbonate → HCID 10626061, compound

Participants

Reaction Steps

To a solution of 2-(4-methoxyphenyl)-3-[N-(4-hydroxyphenyl)acetamido]-6-methoxy-benzo[b]thiophene (1.31 g, 3.13 mmol) and Cs2CO3 (4.10 g, 12.50 mmol) in 15 mL of anhydrous DMF was added 2-chlorethylpiperidine hydrochloride (1.15 g, 6.26 mmol). The resulting mixture was stirred vigorously at room temperature for 5 h. The reaction mixture was diluted with 200 mL of H2O, and then extracted several times with EtOAc. The combined organic was then washed with H2O several times and then dried (Na2SO4), Concentration in vacuo provided an oil. Chromatography (1% CH3OH/CHCl3, SiO2) provided 1.49 g (90%) of 2-(4-methoxyphenyl-3-[N-[4-[2-(1-piperidinyl)ethoxy]phenyl]acetamido]-6-methoxybenzo[b]thiophene as an amber oil. 1H NMR (DMSO-d6) δ (doubling due to amide rotamers) 7.66-6.70 (m, 11 H), 3.93 (m, 2H) 3.78 and 3.58 (s, 6H), 2.8-2.30 (m, 6H), 2.01 and 1.78 (s, 3H), 1.52-1.11 (m, 6H). FD mass spec: 530. Anal. Calcd. for C31H34N2O4S: C, 70.16; H, 6.46; N, 5.28. Found: C, 70.33; H, 6.34; N, 5.35.

Provenance & Evidence