Reaktion #82490

Reaktionsgleichung

3-dimethylaminomethyl-1H-pyrrolo[2,3-b]pyridine

1-(5-indolyl)piperazine

→

title compound

Ausbeute 32.0%

3-(4-[5-Indolyl]piperazin-1-yl)methyl-1H-pyrrolo [2,3-b]pyridine

Ausbeute 32.0%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturat reflux for 16 h under nitrogen
3. 3
   Temperaturto cool
4. 4
   SonstigePurification by flash chromatography
5. 5
   Wascheneluting with 90:8:1 dichloromethane/methanol/ammonia

Vorschrift

A mixture of 3-dimethylaminomethyl-1H-pyrrolo[2,3-b]pyridine (0.23 g, 1.33 mmol) and 1-(5-indolyl)piperazine (0.27 g, 1.34 mmol) in toluene (20 ml) was heated at reflux for 16 h under nitrogen. The mixture was allowed to cool and the solid present collected. Purification by flash chromatography, eluting with 90:8:1 dichloromethane/methanol/ammonia, twice gave the title compound (0.14 g, 32%) as a white solid. Recrystallisation from methanol afforded needles, m.p. 232.5°-233° C.; (Found: C, 72.14; H, 6.29; N, 21.07. C20H21N5. 0.1H2O requires C, 72.09; H, 6.41; N, 21.02%); δH (DMSO-d6) 2.56 (4H, m, 2×piperazinyl CH2), 3.02 (4H, m, 2×piperazinyl CH2), 3.69 (1H, s, CH2N), 6.27 (1H, m, 3'-H), 6.83 (1H, dd, J 8.8, 2.1 Hz, 6'-H), 6.97 (1H, m, 2'-H), 7.05 (1H, dd, J 7.8, 4.6 Hz, 5-H), 7.22 (2H, m, 4'-H, 7'-H), 7.38 (1H, d, J 2.1 Hz, 2-H), 8.06 (1H, dd, J 7.8, 1.4 Hz, 4-H), 8.20 (1H, dd, J 4.6, 1.4 Hz, 6-H), 10.77 (1H, br s, NH), and 11.46 (1H, br s NH); m/z (CI+, NH3) 322 (M+1)+.

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