Reaktion #548725

Reaktionsgleichung

hydrogen chloride

3-benzoyloxy-1,2,3,4-tetrahydrocarbazole

sodium hydride

3-benzoyloxy-1,2,3,4-tetrahydrocarbazole hydrochloride

3-(dimethylamino)propyl chloride

→

3-benzoyloxy-9-[3-(dimethylamino)propyl]-1,2,3,4-tetrahydrocarbazole

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe crude free base was extracted from the water
2. 2
   workup.ADDITIONdiluted
3. 3
   Sonstigereaction mixture into ether
4. 4
   SonstigeThe resulting precipitate was recrystallized from isopropyl alcohol and ethyl acetate
5. 5
   Sonstigeto give 6.2 g

Vorschrift

The 3-benzoyloxy-9-[3-(dimethylamino)propyl]-1,2,3,4-tetrahydrocarbazole was prepared by following an alkylation procedure similar to that described in Example 11 and using 29.1 g. of 3-benzoyloxy-1,2,3,4-tetrahydrocarbazole and 4.3 g. of sodium hydride (50% in mineral oil) in 200 ml. of dimethylformamide, and 13 g. of 3-(dimethylamino)propyl chloride. The crude free base was extracted from the water diluted reaction mixture into ether and the ethereal solution was treated with ethereal hydrogen chloride. The resulting precipitate was recrystallized from isopropyl alcohol and ethyl acetate to give 6.2 g. of 3-benzoyloxy-1,2,3,4-tetrahydrocarbazole hydrochloride, m.p. 162°-180° C.

Quelle