1-(4-Ethoxyphenyl)piperazine → 3-(4-[4-Ethoxyphenyl]piperazin-1-yl)methyl-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Steps

A mixture of 3-dimethylaminomethyl-1H-pyrrolo[2,3-b]pyridine [prepared by the method of M. M. Robinson and B. L. Robinson, J. Am. Chem. Soc., 1955, 77, 457] (0.40 g, 2.28 mmol) and 1-(4-ethoxyphenyl)piperazine (0.495 g, 2.40 mmol) in toluene (10 ml) was heated at reflux under nitrogen for 7 h. The mixture was allowed to cool and the crystallised product collected. Recrystallisation from methanol afforded the title compound (0.513 g, 67%), m.p. 179°-180° C.; (Found: C, 71.27; H, 7.19; N, 16.59. C20H24N4O requires C, 71.40; H, 7.19; N, 16.65%); δH (DMSO-d6) 1.27 (3H, t, J 7.0 Hz, ArOCH2CH3), 2.52 (4H, m, 2×piperazinyl CH2), 2.98 (4H, m, 2×piperazinyl CH2), 3.67 (2H, s, CH2N), 3.92 (2H, q, J 7.0 Hz, ArOCH2CH3), 6.80 (4H, m, ArH), 7.04 (1H, dd, J 7.8, 4.6 Hz, 5-H), 7.37 (1H, d, J 2.1 Hz, 2-H), 8.04 (1H, dd, J 7.8, 1.3 Hz, 4-H), 8.19 (1H, dd, J 4.6, 1.3 Hz, 6-H), and 11.46 (1H, br s, NH); m/z (CI+, NH3) 337 (M+1)+.

Provenance & Evidence