Toluene → 4-[3-(4-Methyl-1-piperazinyl)propyl]-4-azatricyclo[4.3.1.13,8]undecan-5-one

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Reaction Steps

To a well stirred solution of 2.4 gm. (0.02 mole) of 4-azatricyclo[4.3.1.13,8 ]undecan-5-one in 300 ml. of toluene, 3.2 gm. of powdered sodium hydroxide are added. After 5 minutes of vigorous stirring, 12 gm. of 1-(3-bromopropyl)-4-methylpiperazine dihydrobromide are added and the mixture heated for 20 minutes on a steam bath. The reaction mixture is cooled and stirred with 50 ml. of cold water. The toluene layer is separated, washed with 2 × 50 ml. of water and extracted with 3 × 100 ml. of 5 N HCl. The acid extracts are combined, washed with 100 ml. of ether, cooled and made basic with 2 N NaOH. The free base is extracted with 3 × 250 ml. of chloroform, dried (MgSO4) and evaporated in vacuo to give 4-[3-(4-methyl-1-piperazinyl)propyl]-4-azatricyclo[4.3.1.13,8 ]undecan-5-one.

Provenance & Evidence