3,8-Dioxabicyclo[3.2.1]octane-2,4-dione → 3-[4-[4-(6-Chloro-2-pyrazinyl)-1-piperazinyl]butyl]-8-oxa-3-azabicyclo[3.2.1]octane-2,4-dione

HRID 1253265노트

반응식

HRID 1253265 반응식
[O:1]1[CH:5]2[C:6]([O:8][C:9](=[O:10])[CH:2]1[CH2:3][CH2:4]2)=O.[NH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:27]=[N:26][CH:25]=[C:24]([Cl:28])[N:23]=2)[CH2:18][CH2:17]1>C(Cl)Cl>[Cl:28][C:24]1[N:23]=[C:22]([N:19]2[CH2:18][CH2:17][N:16]([CH2:15][CH2:14][CH2:13][CH2:12][N:11]3[C:6](=[O:8])[CH:5]4[O:1][CH:2]([CH2:3][CH2:4]4)[C:9]3=[O:10])[CH2:21][CH2:20]2)[CH:27]=[N:26][CH:25]=1

참가 물질

4

반응물 2

HCID 134257993,8-Dioxabicyclo[3.2.1]octane-2,4-dioneHCID 140865264-[4-(6-Chloropyrazin-2-yl)piperazin-1-yl]butan-1-amine

생성물 1

HCID 141563713-[4-[4-(6-Chloro-2-pyrazinyl)-1-piperazinyl]butyl]-8-oxa-3-azabicyclo[3.2.1]octane-2,4-dione

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Tetrahydrofuran-2,5-dicarboxylic anhydride (1.26 g., 8.8 mmole) and 1-(4-aminobutyl)-4-(6-chloro-2-pyrazinyl)piperazine (2.37 g., 8.8 mmole) were combined and stirred for 30 minutes in 200 ml. of methylene chloride. The solvent was removed in vacuum and replaced with 300 ml. of xylene. The mixture as refluxed for 48 hours with water removal via a Dean-Stark trap. After cooling, the mixture was filtered through 75 g. of silica gel and the column rinsed with 5% ethanol/chloroform. The product was concentrated in vacuum and recrystallized from isopropanol with addition of 4N isopropanolic HCl. 0.60 Grams of the title compound was obtained as the monohydrochloride; m.p. 233°-235° C. (d).

후처리

  1. customThe solvent was removed in vacuum
  2. temperatureThe mixture as refluxed for 48 hours with water removal via a Dean-Stark trap
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered through 75 g
  5. washof silica gel and the column rinsed with 5% ethanol/chloroform
  6. concentrationThe product was concentrated in vacuum
  7. customrecrystallized from isopropanol with addition of 4N isopropanolic HCl

출처 및 근거

ORD 기록
ord-9da688d532494728b3fdbb0b3f23bb24
출처 데이터셋
uspto-grants-1988_05
특허 번호
US04748240

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