Sodium Carbonate → 6-[2-[4-[bis(4-fluorophenyl)methylene]-1-piperidinyl]ethyl]-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one

Participants

Reaction Steps

A mixture of 5.6 parts of 6-(2-bromoethyl)-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one monohydrobromide, 3.5 parts of 4-[bis(4-fluorophenyl)methylene]piperidine, 1 part of a sodium methoxide solution 30%, 8 parts of sodium carbonate and 240 parts of 4-methyl-2-pentanone was stirred and refluxed for 20 hours using a water-separator. The reaction mixture was filtered while hot and the filtrate was evaporated. The residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from acetonitrile, yielding 4.3 parts (72.8%) of 6-[2-[4-[bis(4-fluorophenyl)methylene]-1-piperidinyl]ethyl]-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one; mp. 183.8° C. (compound 112).

Provenance & Evidence