Dibenzosuberol → Oxitriptyline

HRID 1900249노트

반응식

HRID 1900249 반응식
[H-].[Na+].[CH2:3]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]([OH:18])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4]1.Cl[CH2:20][C:21]([N:23]([CH3:25])[CH3:24])=[O:22]>CCCCCC.CCOCC>[CH:16]1[C:17]2[CH2:3][CH2:4][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=3[CH:11]([O:18][CH2:20][C:21]([N:23]([CH3:25])[CH3:24])=[O:22])[C:12]=2[CH:13]=[CH:14][CH:15]=1

참가 물질

6

반응물 3

HCID 14588DibenzosuberolHCID 24758Sodium hydrideHCID 758862-chloro-N,N-dimethylacetamide

생성물 1

HCID 34624Oxitriptyline수율 72.3%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매3회HCID 8058Hexane용매

실험 절차

Washed sodium hydride (2.6 g, 64.6 mmol, 60 weight % in oil) two times with hexane under a nitrogen atmosphere. Added 50 mL of dry ether, and then added dibenzosuberol (13.6 g, 64.6 mmol) dissolved in 30 mL of dry ether followed by 2-chloro-N,N-dimethylacetamide (7.8 g, 64.6 mmol) dissolved in 20 mL of dry ether. Stirred at room temperature for 16 hours. Added water, and separated layers. Evaporated the organic solution, and triturated the residue with carbon tetrachloride and hexane. Filtered the white solid to give 13.79 g (72% yield) of 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl-oxy-N,N-dimethylacetamide.

후처리

  1. customAdded water, and separated layers
  2. customEvaporated the organic solution
  3. customtriturated the residue with carbon tetrachloride and hexane
  4. filtrationFiltered the white solid

출처 및 근거

ORD 기록
ord-ba38d220116b4c5a8607969808d79758
출처 데이터셋
uspto-grants-1996_11
특허 번호
US05574173

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