Pyridine → N-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]acetamide

HRID 2106780

반응식

HRID 2106780 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.N1C=CC=CC=1.CN(C)C=O.[C:32](Cl)(=[O:34])[CH3:33]>O.CC1C=CC=CC=1>[OH:20][C:17]1[CH:18]=[CH:19][C:14]([N:11]2[CH2:12][CH2:13][N:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:32](=[O:34])[CH3:33])=[CH:7][CH:6]=3)[CH2:9][CH2:10]2)=[CH:15][CH:16]=1

참가 물질

7

반응물 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 6367Acetyl chlorideHCID 102210654-[4-(4-Aminophenyl)piperazin-1-yl]phenol

생성물 1

HCID 15125497N-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]acetamide수율 42.5%

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

실험 절차

To a stirred solution of 10.8 parts of 4-[4-(4-aminophenyl)-1-piperazinyl]phenol in 3.2 parts of pyridine and 90 parts of N,N-dimethylformamide was added dropwise a solution of 3.1 parts of acetyl chloride in 27 parts of methylbenzene at 20° C. (exothermic reaction). Upon completion, stirring was continued for 1 hour at 20° C. The reaction mixture was poured into water while stirring. The product was filtered off, washed with water and dissolved in a mixture of trichloromethane and methanol (3:1 by volume). The whole was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The second fraction was collected and the eluent was evaporated. The residue was crystallized from a mixture of ethanol and methylbenzene (1:1 by volume)+(activated charcoal). The produce was filtered off and dried yielding 5.3 parts (42.5%) of N-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]acetamide; mp. 256.2° C. (compound 1.03).

후처리

  1. custom(exothermic reaction)
  2. stirringwhile stirring
  3. filtrationThe product was filtered off
  4. washwashed with water
  5. dissolutiondissolved in a mixture of trichloromethane and methanol (3:1 by volume)
  6. customThe whole was purified by column chromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  8. customThe second fraction was collected
  9. customthe eluent was evaporated
  10. customThe residue was crystallized from a mixture of ethanol and methylbenzene (1:1 by volume)+(activated charcoal)
  11. filtrationThe produce was filtered off
  12. customdried

출처 및 근거

ORD 기록
ord-ba3575adee5644449488737b02f2352a
출처 데이터셋
uspto-grants-1990_06
특허 번호
US04931444

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