反応 #4412

反応方程式

sodium hydroxide

1-(4-chlorobenzyl)piperazine

malonyl dichloride

methylene chloride

→

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

収率 45.1%

溶媒

triethylamine

反応条件

後処理

1. 1
   その他The organic layer was separated
2. 2
   抽出the aqueous phase was extracted with three 50 ml portions of ether
3. 3
   workup.ADDITIONmixed with 100 ml of 2N hydrochloric acid
4. 4
   その他The aqueous phase was separated
5. 5
   その他The resulting oil was collected
6. 6
   その他chromatographed on silica
7. 7
   その他evaporated to an oil
8. 8
   workup.DISSOLUTIONdissolved in 100 ml of ether
9. 9
   その他precipitated with excess anhydrous hydrogen chloride
10. 10
    その他The precipitate was recrystallized from reagent ethanol

実験手順

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.).

出典