Dichloromethane → 1,3-Bis[4-(4-chlorobenzyl)-1-piperazinyl]-1,3-dioxopropane dihydrochloride monohydrate

HRID 4316

반응식

HRID 4316 반응식
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[C:15](Cl)(=[O:20])[CH2:16][C:17]([Cl:19])=[O:18].[CH2:22]([Cl:24])Cl.[OH-].[Na+]>C(N(CC)CC)C>[OH2:18].[ClH:1].[ClH:19].[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][N:10]([C:15](=[O:20])[CH2:16][C:17]([N:10]3[CH2:11][CH2:12][N:7]([CH2:6][C:5]4[CH:13]=[CH:14][C:22]([Cl:24])=[CH:3][CH:4]=4)[CH2:8][CH2:9]3)=[O:18])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 74269Propanedioyl dichlorideHCID 1348264-Chlorobenzylpiperazine

생성물 1

HCID 201522271,3-Bis[4-(4-chlorobenzyl)-1-piperazinyl]-1,3-dioxopropane dihydrochloride monohydrate수율 45.1%

시약·촉매·용매 1

HCID 8471Triethylamine용매

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.).

후처리

  1. customThe organic layer was separated
  2. extractionthe aqueous phase was extracted with three 50 ml portions of ether
  3. additionmixed with 100 ml of 2N hydrochloric acid
  4. customThe aqueous phase was separated
  5. customThe resulting oil was collected
  6. customchromatographed on silica
  7. customevaporated to an oil
  8. dissolutiondissolved in 100 ml of ether
  9. customprecipitated with excess anhydrous hydrogen chloride
  10. customThe precipitate was recrystallized from reagent ethanol

출처 및 근거

ORD 기록
ord-5fbf8b934342464383a21037ee00b589
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04725597

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