Ethanol → 5-Amino-2-[4-(2-hydroxyethyl)piperazin-1-yl]benzonitrile

HRID 1744500

반응식

HRID 1744500 반응식
[Cl-].[NH4+].O.[N+:4]([C:7]1[CH:8]=[CH:9][C:10]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH:16]2CCO)=[C:11]([CH:14]=1)[C:12]#[N:13])([O-])=O.[CH2:24]([OH:26])[CH3:25]>[Fe]>[NH2:4][C:7]1[CH:8]=[CH:9][C:10]([N:15]2[CH2:16][CH2:17][N:18]([CH2:25][CH2:24][OH:26])[CH2:19][CH2:20]2)=[C:11]([CH:14]=1)[C:12]#[N:13]

참가 물질

6

반응물 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 222281915-Nitro-2-(2-hydroxyethylpiperazin-1-yl)benzonitrile

생성물 1

HCID 176095935-Amino-2-[4-(2-hydroxyethyl)piperazin-1-yl]benzonitrile

시약·촉매·용매 1

HCID 23925Iron촉매

반응 조건

온도
65 °C

실험 절차

Ammonium chloride (1.5 g) and iron powder (13.8 g) were added to a mixed solvent of water (51 ml) and ethanol (170 ml), and the mixture was heated to 65° C. Then, 5-nitro-2-(2-hydroxyethylpiperazin-1-yl)benzonitrile (17 g) was added in parts over 20 min and the mixture was stirred at a refluxing temperature for 30 min. The reaction mixture was ice-cooled and filtrated. The solvent was evaporated under reduced pressure. To the residue was added aqueous sodium hydroxide solution and the mixture was extracted with toluene. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, after which the solvent was evaporated under reduced pressure. Diisopropyl ether was added to the residue to allow crystallization. The crystals were recrystallized from a mixed solvent of ethyl acetate-n-hexane to give the title compound (13 g), melting point: 137–138° C.

후처리

  1. temperaturecooled
  2. filtrationfiltrated
  3. customThe solvent was evaporated under reduced pressure
  4. additionTo the residue was added aqueous sodium hydroxide solution
  5. extractionthe mixture was extracted with toluene
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customafter which the solvent was evaporated under reduced pressure
  9. additionDiisopropyl ether was added to the residue
  10. customcrystallization
  11. customThe crystals were recrystallized from a mixed solvent of ethyl acetate-n-hexane

출처 및 근거

ORD 기록
ord-bb76e86d84194135823f66ec752931f3
출처 데이터셋
uspto-grants-2006_03
특허 번호
US07015218B1

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