반응 #4412

반응 방정식

sodium hydroxide

1-(4-chlorobenzyl)piperazine

malonyl dichloride

methylene chloride

→

1,3-bis[4-(4 -chlorobenzyl)-1-piperazinyl]-1,3-dioxopropane dihydrochloride monohydrate

수율 45.1%

용매

triethylamine

반응 조건

후처리

1. 1
   기타The organic layer was separated
2. 2
   추출the aqueous phase was extracted with three 50 ml portions of ether
3. 3
   workup.ADDITIONmixed with 100 ml of 2N hydrochloric acid
4. 4
   기타The aqueous phase was separated
5. 5
   기타The resulting oil was collected
6. 6
   기타chromatographed on silica
7. 7
   기타evaporated to an oil
8. 8
   workup.DISSOLUTIONdissolved in 100 ml of ether
9. 9
   기타precipitated with excess anhydrous hydrogen chloride
10. 10
    기타The precipitate was recrystallized from reagent ethanol

실험 절차

A mixture of 4.2 g of 1-(4-chlorobenzyl)piperazine, 1.4 g of malonyl dichloride, 10 g of methylene chloride and 2.0 g of triethylamine was stirred for 60 hours. The reaction mixture was made basic with 2N sodium hydroxide. The organic layer was separated, and the aqueous phase was extracted with three 50 ml portions of ether, followed by three 50 ml portions of methylene chloride. The organic phases were combined and mixed with 100 ml of 2N hydrochloric acid. The aqueous phase was separated and made basic with 2N sodium hydroxide solution. The resulting oil was collected and chromatographed on silica, the eluant being CH2Cl2 /CH2OH/ammonium hydroxide (200:5:1). The appropriate fractions were combined, evaporated to an oil, dissolved in 100 ml of ether and precipitated with excess anhydrous hydrogen chloride. The precipitate was recrystallized from reagent ethanol to yield 1.3 g (22% of theory) of 1,3-bis[4-(4 -chlorobenzyl)-1-piperazinyl]-1,3-dioxopropane dihydrochloride monohydrate as a very slightly yellow crystalline solid (m.p. 199°-206° C.).

출처