تفاعل #82492

معادلة التفاعل

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

sodium hydroxide

→

title compound

المردود 67.0%

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

المردود 67.0%

المذيبات

ethanol

ظروف التفاعل

المعالجة

1. 1
   workup.DISSOLUTIONslowly dissolved
2. 2
   تركيزThe reaction mixture was concentrated to a small volume
3. 3
   workup.ADDITIONdiluted with water and neutralised (pH 6-7) with acetic acid
4. 4
   أخرىto give a gum which
5. 5
   أخرىThe solid was collected
6. 6
   غسيلwashed with water
7. 7
   أخرىdried in vacuo
8. 8
   أخرىRecrystallisation from dimethylformamide/water

الإجراء التجريبي

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)+.

المصدر