반응 #11184

반응 방정식

bromide

6-(3-Bromopropyl)-9-hydroxy-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

hydrochloric acid

potassium carbonate

dimethylamine

→

amine

수율 47.0%

6-[3-(Dimethylamino)propyl]-9-hydroxy-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

수율 47.0%

용매

water

dimethylacetamide

반응 조건

후처리

1. 1
   기타The reaction vessel was sealed
2. 2
   여과The precipitated product was either collected by filtration
3. 3
   세척washed with water and diisopropyl ether
4. 4
   기타before being dried
5. 5
   추출extracted with ethyl acetate
6. 6
   기타The organic layer was dried
7. 7
   기타the drying agent was removed
8. 8
   농축the solution was concentrated to dryness

실험 절차

To a solution of bromide (204) prepared as described in example 173 (0.12 g, 0.27 mmol) in dimethylacetamide (4 mL) was added the amine, dimethylamine (25 mol eq., 0.85 mL in this case as an 40% aqueous solution). The reaction vessel was sealed and heated at 80° C. with stirring for 18 h, before being diluted with water. The resulting solution was then acidified by the dropwise addition of concentrated hydrochloric acid and the pH was then adjusted to approximately pH=9 by the addition of solid potassium carbonate. The precipitated product was either collected by filtration and washed with water and diisopropyl ether before being dried or extracted with ethyl acetate. The organic layer was dried, the drying agent was removed and the solution was concentrated to dryness. Chromatography on silica eluting with methanol/dichloromethane (1:9 to 1:4), followed by trituration in ethyl acetate/hexane gave amine (208) (52 mg, 47%) as a yellow powder, mp 185–189° C. 1H NMR δ [(CD3)2SO] 11.05 (s, 1H), 9.34 (s, 1H), 8.41 (d, J=2.4 Hz, 1H), 7.78 (s, 1H), 7.64 (m, 2H), 7.56 (d, J=8.9 Hz, 1H), 7.47 (m, 3H), 7.14 (dd, J=8.9, 2.4 Hz, 1H), 4.48 (t, J=6.6 Hz, 2H), 2.16 (t, J=6.5 Hz, 2H), 2.08 (s, 6H), 1.90 (m, 2H). Found: C, 71.98; H, 5.67; N, 10.14. C25H23N3O3.1/4H2O requires: C, 71.84; H, 5.67; N, 10.05.

출처