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

HRID 514783

反応式

HRID 514783 の反応式
[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

参加物

7

反応物 4

HCID 24758Sodium hydrideHCID 3017050Pyrrolidine, 2-(2-chloroethyl)-1-methyl-, hydrochloride (1:1)HCID 21584188Chloroform methanolHCID 58544896HCID 58544896、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6386de38e7034ad98a8451b6cdda36dc
出典データセット
uspto-grants-2015_08
特許番号
US09108916B2

関連ノート

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