反应详情

In 10 ml of chloroform was suspended 2.5 g (10.5 millimoles) of 2,3,4-trimethoxycinnamic acid, and under ice cooling, 3.5 ml (about 48 millimoles) of thionyl chloride was added dropwise. The mixture was stirred for 30 minutes under ice cooling, and the excess of thionyl chloride and chloroform were distilled off under reduced pressure. The residue was diluted with 20 ml of methylene chloride and added dropwise under ice cooling to 30 ml of a methylene chloride solution of 2.7 g (9.4 millimoles) of bis(4-fluorophenyl)methylpiperazine and 2 g (19.8 millimoles) of triethylamine. The mixture was stirred for 30 minutes under ice cooling. Thereafter, a 10% aqueous solution of sodium bicarbonate was added, and the mixture was shaken. The organic layer was separated, washed with water, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The resulting oily product was diluted with 20 ml of ethanol. One milliliter of concentrated hydrochloric acid was added and then ether was added. The crystals that precipitated were collected by filtration. Recrystallization from methanol gave 1.4 g (yield 27.3%) of 1-[bis(4-fluorophenyl)methyl]-4-(2,3,4-trimethoxycinnamoyl)piperazine hydrochloride as colorless crystals.

1. distillationthe excess of thionyl chloride and chloroform were distilled off under reduced pressure
2. additionThe residue was diluted with 20 ml of methylene chloride
3. stirringThe mixture was stirred for 30 minutes under ice cooling
4. stirringthe mixture was shaken
5. customThe organic layer was separated
6. washwashed with water
7. dry with materialdried over anhydrous magnesium sulfate
8. distillationThe solvent was distilled off under reduced pressure
9. additionThe resulting oily product was diluted with 20 ml of ethanol
10. additionOne milliliter of concentrated hydrochloric acid was added
11. additionether was added
12. customThe crystals that precipitated
13. filtrationwere collected by filtration
14. customRecrystallization from methanol