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Water → Agomelatine

HRID 243637
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HRID 243637 반응식
Cl.[CH3:2][O:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[C:11]2[CH2:14][CH2:15][NH2:16])=[CH:6][CH:5]=1.[C:17]([O-])(=[O:19])[CH3:18].[Na+].C(OC(=O)C)(=O)C.O>C(O)C>[CH3:18][C:17]([NH:16][CH2:15][CH2:14][C:11]1[C:12]2[CH:13]=[C:4]([O:3][CH3:2])[CH:5]=[CH:6][C:7]=2[CH:8]=[CH:9][CH:10]=1)=[O:19]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 160500552-(7-Methoxynaphthalen-1-yl)ethan-1-amine hydrochloride

생성물 1

HCID 82148Agomelatine수율 86.7%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

The compound V (6.0 g, 0.03 mol) produced as described above and sodium acetate (3.4 g) were dissolved in 70 ml of ethanol, and acetic anhydride (3.4 g, 0.033 mol) was added. The reaction solution was heated and refluxed for one hour. After cooling, about 100 ml of water was added, and the mixture was extracted with ethyl acetate (50 ml*3). The organic phases were combined, dried with anhydrous magnesium sulfate, and filtered to remove the drying agent. The filtrate was concentrated under reduced pressure, to give a solid. The solid was recrystallized in a 2:1 toluene/n-hexane mixture, to produce 5.3 g of agomelatine. The yield was 86.7%. The melting point was 108-109° C. (in Literature [2], 109° C.).

후처리

  1. temperatureThe reaction solution was heated
  2. temperaturerefluxed for one hour
  3. temperatureAfter cooling
  4. extractionthe mixture was extracted with ethyl acetate (50 ml*3)
  5. dry with materialdried with anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customto remove the drying agent
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customto give a solid
  10. customThe solid was recrystallized in a 2:1 toluene/n-hexane mixture

출처 및 근거

ORD 기록
ord-c33808f410004f548ba8af3da2641b19
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08653281B2

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