反应详情

A suspension of 3-(4-[4-ethoxycarbonylphenyl]piperazin-1-yl)methyl-1H-pyrrolo[2,3-b]pyridine (0.6594 g, 1.81 mmol) in ethanol (50 ml) containing 1M aqueous sodium hydroxide (10.5 ml, 10.8 mmol) was stirred at room temperature for eight days, during which time the solid slowly dissolved. The reaction mixture was concentrated to a small volume, diluted with water and neutralised (pH 6-7) with acetic acid to give a gum which solidified on standing. The solid was collected, washed with water and dried in vacuo. Recrystallisation from dimethylformamide/water gave the title compound (0.4069 g, 67%) as a white solid, m.p. >250° C. (dec.); (Found: C, 66.96; H, 5.88; N, 16.30. C19H20N4O2.0.25H2O requires C, 66.94; H, 6.06; N, 16.44); δH (DMSO-d6) 2.51 (4H, m, 2×piperazinyl CH2), 3.27 (4H, m, 2×piperazinyl CH2), 3.68 (2H, s, CH2N), 6.93 (2H, d, J 9.0 Hz, ArH), 7.04 (1H, dd, J 7.8, 4.7 Hz, 5-H), 7.38 (1H, d, J 2.2 Hz, 2-H), 7.57 (2H, d, J 9.0 Hz, ArH), 8.06 (1H, dd, J 7.8, 1.4 Hz, 4-H), 8.20 (1H, dd, J 4.7, 1.4 Hz, 6-H), and 11.48 (1H, br s, NH); m/z (CI+, NH3) 337 (M+1)+.

1. dissolutionslowly dissolved
2. concentrationThe reaction mixture was concentrated to a small volume
3. additiondiluted with water and neutralised (pH 6-7) with acetic acid
4. customto give a gum which
5. customThe solid was collected
6. washwashed with water
7. customdried in vacuo
8. customRecrystallisation from dimethylformamide/water