Sodium hydride → 6-[2-(1-methylpyrrolidin-2-yl)ethyl]-1,6-dihydrocyclopenta[c]carbazol-3(2H)-one

HRID 1615032노트

반응식

HRID 1615032 반응식
[CH2:1]1[C:16]2[C:15]3[C:14]4[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=4[NH:8][C:7]=3[CH:6]=[CH:5][C:4]=2[C:3](=[O:17])[CH2:2]1.[H-].[Na+].Cl.Cl[CH2:22][CH2:23][CH:24]1[CH2:28][CH2:27][CH2:26][N:25]1[CH3:29].C(Cl)(Cl)Cl.CO>C(Cl)Cl.O>[CH3:29][N:25]1[CH2:26][CH2:27][CH2:28][CH:24]1[CH2:23][CH2:22][N:8]1[C:7]2[CH:6]=[CH:5][C:4]3[C:3](=[O:17])[CH2:2][CH2:1][C:16]=3[C:15]=2[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]1=2

참가 물질

7

반응물 4

HCID 24758Sodium hydrideHCID 3017050Pyrrolidine, 2-(2-chloroethyl)-1-methyl-, hydrochloride (1:1)HCID 21584188Chloroform methanolHCID 585448961,6-Dihydrocyclopenta[c]carbazol-3(2H)-one

생성물 1

HCID 585449036-[2-(1-methylpyrrolidin-2-yl)ethyl]-1,6-dihydrocyclopenta[c]carbazol-3(2H)-one

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

Carbazole 46 (0.4 g, 1.81 mmol) was dissolved in CH2Cl2 (7 mL), then NaH (0.22 g, 5.50 mmol) was added. The mixture was stirred at room temperature for 5-10 min, and 2-(2-chloroethyl)-1-methylpyrrolidine hydrochloride (0.4 g, 2.17 mmol) was added. The mixture was heated to 60° C. and kept at this temperature for 4 h (TLC monitoring, eluent: CHCl3-MeOH, 9:1). The resulting mixture was poured into water. The product was extracted with ethyl acetate, dried over Na2SO4, and evaporated. The residue was triturated with ether. The precipitate was filtered off. Yield of 65: 0.365 g (61%)—S-isomer and 0.336 g (55%)—R-isomer.

후처리

  1. temperatureThe mixture was heated to 60° C.
  2. waitkept at this temperature for 4 h
  3. extractionThe product was extracted with ethyl acetate
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue was triturated with ether
  7. filtrationThe precipitate was filtered off

출처 및 근거

ORD 기록
ord-fba698b804b14d39a1478d026d78780a
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765738B2

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