Dimethylformamide → 1-(4-Hydroxyphenyl)-4-(1-phthalazinyl)piperazine

HRID 621508

반응식

HRID 621508 반응식
Br.Br.[OH:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1.Cl[C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[N:19][N:18]=1.C([O-])([O-])=O.[K+].[K+].CN(C=O)C>C(Cl)Cl>[OH:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=[N:19][N:18]=3)[CH2:12][CH2:11]2)=[CH:8][CH:9]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium Carbonate3회HCID 1607931-ChlorophthalazineHCID 2723591p-(1-Piperazinyl)phenol dihydrobromide

생성물 1

HCID 140741161-(4-Hydroxyphenyl)-4-(1-phthalazinyl)piperazine수율 15.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
85 °C

실험 절차

A mixture of 5.11 g (15 mmol) of 1-(4-hydroxyphenyl)piperazine dihydrobromide, 2.48 g (15 mmol) of 1-chlorophthalazine, 2.08 g (15 mmol) of powdered K2CO3 and 55 ml of absolute DMF was warmed to 85° C., and 346 mg of powdered K2CO3 were added at 85° C. with stirring in each case after 10 minutes, after a further 25 minutes and after a further 60 minutes (a total of 1.038 g, 7.51 mmol of K2CO3), and the mixture was stirred for a further 2 hours at 90° C. and 3 hours at 105° C. The DMF was then removed by distillation in vacuo, the residue was taken up in CH2Cl2 /water, the phases were separated after through mixing, and the aqueous solution was extracted three times with CH2Cl2. The combined CH2Cl2 extracts were dried, filtered and evaporated in vacuo. The residue remaining (4.75 g) was chromatographed on a silica gel S/CH2Cl2 column (diameter 2.6 cm, height 43 cm) by elution with CH2Cl2 /C2H5OH mixtures with increasing C2H5OH content (1-10% by volume). The fractions in which, according to TLC, the required compound was concentrated were combined and evaporated. The crystalline residue produced (2.04 g) was boiled briefly with 15 ml of CH2Cl2, cooled in an ice bath, and filtered off under suction. 0.73 g of pure 1-(4-hydroxyphenyl)-4-(1-phthalazinyl)piperazine, melting point 244°-45° C., were thus obtained. The mother liquor was again purified by chromatography in analogous fashion to the first column chromatography on a silica gel/CH2Cl2 column (diameter 2.0 cm, height 22 cm). The concentrated product produced from this procedure was, like the first part, boiled briefly with 7 ml of CH2Cl2 and filtered off under suction when cool. A further 0.28 g of pure compound, melting point 244°-45° C., was obtained from this procedure. The total yield was 1.01 g=22% of theory;

후처리

  1. customThe DMF was then removed by distillation in vacuo
  2. customthe phases were separated after
  3. additionthrough mixing
  4. extractionthe aqueous solution was extracted three times with CH2Cl2
  5. dry with materialThe combined CH2Cl2 extracts were dried
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customwas chromatographed on a silica gel S/CH2Cl2 column (diameter 2.6 cm, height 43 cm) by elution with CH2Cl2 /C2H5OH
  9. concentrationthe required compound was concentrated
  10. customevaporated
  11. customThe crystalline residue produced (2.04 g)
  12. temperaturecooled in an ice bath
  13. filtrationfiltered off under suction

출처 및 근거

ORD 기록
ord-71b4c3be899b46dd900f3e472307249a
출처 데이터셋
uspto-grants-1989_04
특허 번호
US04824846

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