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Carbazole → 6-[3-(Dimethylamino)propyl]-8-methoxy-1,6-dihydrocyclopenta[c]carbazol-3(2H)-one

HRID 514761
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인쇄 미리보기

반응식

HRID 514761 반응식
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]3[C:8]4[CH2:18][CH2:17][C:16](=[O:19])[C:9]=4[CH:10]=[CH:11][C:12]=3[NH:13][C:14]=2[CH:15]=1.[H-].[Na+].Cl.[CH3:23][N:24]([CH3:29])[CH2:25][CH2:26][CH2:27]Cl.C1C2NC3C(=CC=CC=3)C=2C=CC=1>C(Cl)Cl.O.C(Cl)(Cl)Cl.CO.C(Cl)Cl.C(OCC)(=O)C>[CH3:23][N:24]([CH3:29])[CH2:25][CH2:26][CH2:27][N:13]1[C:12]2[CH:11]=[CH:10][C:9]3[C:16](=[O:19])[CH2:17][CH2:18][C:8]=3[C:7]=2[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:15][C:14]1=2
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 4

HCID 6854CarbazoleHCID 24758Sodium hydrideHCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 709006108-Methoxy-1,6-dihydrocyclopenta[c]carbazol-3(2H)-one

생성물 1

HCID 585449126-[3-(Dimethylamino)propyl]-8-methoxy-1,6-dihydrocyclopenta[c]carbazol-3(2H)-one

시약·촉매·용매 4

HCID 962
Water
용매
HCID 6344Dichloromethane용매
HCID 21226138Dichloromethane ethylacetate용매
HCID 21584188Chloroform methanol용매

실험 절차

Compound 36 (1.0 g, 3.98 mmol) was suspended in CH2Cl2 (10 mL); NaH (0.75 g, 12.0 mmol, 3 eq.) was added. The mixture was stirred at room temperature for 5-10 min; then 3-dimethylamino-1-propyl chloride hydrochloride (0.75 g, 4.74 mmol, 1.2 eq.) was added. The reaction mixture was heated to 70° C., kept at this temperature for 2 h (TLC monitoring, eluent: CH2Cl2-ethyl acetate, 1:1—the presence of initial carbazole, CHCl3-MeOH, 9:1—purity of the product). The resulting mixture was diluted with water, extracted with ethyl acetate, evaporated, and purified on a short thick column with silica gel, eluent: CHCl3-MeOH 99:1→90:10. Yield of 37: 0.84 g (63%).

후처리

  1. temperatureThe reaction mixture was heated to 70° C.
  2. waitkept at this temperature for 2 h
  3. extractionextracted with ethyl acetate
  4. customevaporated
  5. custompurified on a short thick column with silica gel, eluent

출처 및 근거

ORD 기록
ord-9862ff80955840c9978f6918bfa2a3fe
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09108916B2

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