1-((5-(p-Chlorophenyl)furfurylidene)amino)-3-(4-(4-methyl-1-piperazinyl)butyl)hydantoin dihydrochloride → 1-[(E)-[5-(4-chlorophenyl)furan-2-yl]methylideneamino]-3-[4-(4-methylpiperazin-1-yl)butyl]imidazolidine-2,4-dione

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Reaction Steps

1-[[[5-(4-Chlorophenyl)-2-furanyl]methylene]amino-3-[4-(4-methyl-1-piperazinyl)butyl]-2,4-imidazolidinedine, a free-base, is prepared as described hereinbelow. The dihydrochloride salt, 1-[[[5-(4-Chlorophenyl)-2-furanyl]methylene]amino]-3-[4-(4-methyl-1-piperazinyl)butyl]-2,4 imidazolidinedione dihydrochloride, (6.56 g, 0.0124 mole) prepared as described in Example A herein, is dissolved in H2O (300 ml) and washed with (1×100 ml). The aqueous phase is made basic with saturated NaHO3 solution. The resulting mixture is extracted with CH2Cl2 (4×100 ml). The extract is washed with saturated NaCl (2×50 ml), dried over MgSO4 (activated charcoal), filtered and concentrated under reduced pressure to a solid residue. This solid is triturated in anhydrous ether, collected and air-dried. Recrystallization once from absolute EtOH and then from toluene (activated charcoal), next washing with anhydrous ether and air drying gives 2.05 g (0.0045 mole) of 1-[[[5-(4-chlorophenyl)-2-furanyl]methylene]amino]-3-[4-(4-methyl-1-piperazinyl)butyl]-2,4-imidazolidinedione.

Provenance & Evidence