Zetidoline
Zetidoline Basic information
- Product Name:
- Zetidoline
- Synonyms:
-
- Zetidoline
- 1-(3-Chlorophenyl)-3-[2-(3,3-dimethylazetidin-1-yl)ethyl]-2-imidazolidinone
- MDL-308
- 2-Imidazolidinone, 1-(3-chlorophenyl)-3-[2-(3,3-dimethyl-1-azetidinyl)ethyl]-
- CAS:
- 51940-78-4
- MF:
- C16H22ClN3O
- MW:
- 307.823
- Mol File:
- 51940-78-4.mol
Zetidoline Usage And Synthesis
Originator
MDL 308 ,Dow Chemical
Manufacturing Process
A solution of 5.0 g of 1-(m-chlorophenyl)-2-imidazolidinone in 30 ml of dimethylformamide is added at room temperature to a mixture of 1.5 g of 50% NaH (mineral oil emulsion) in 30 ml of dimethylformamide. The reaction mixture is stirred for 1 h at room temperature and then 4.5 g of 3,3-dimethyl- 1-(2-chloroethyl)azetidine are added. The mixture is stirred again at room temperature for 2 h and then it is heated for 5 h at 80°-85°C. The salts are filtered off and the solvent is removed under vacuum. The residue is taken up with 8 ml of 18% HCl and 16 ml of water and extracted with diethyl ether. The water solution is alkalinized by addition of 15% sodium carbonate and then extracted with diethyl ether. By evaporation of the organic layer a residue is obtained that is triturated in light petroleum. Yield of 1-(m- chlorophenyl)-3-[2-(3,3-dimethylazetidin-1-y1)ethyl]-2-imidazolidinone 7.25 g, melting point 84°-85°C (after recrystallization from hexane).
Therapeutic Function
Antipsychotic, Neuroleptic