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Acetone → 6-[2-(isopropylamino)ethyl]-10,11-dihydro-1H-dicyclopenta[c,g]carbazole-3,9(2H,6H)-dione

HRID 514778
ノート
印刷プレビュー

反応式

HRID 514778 の反応式
[NH2:1][CH2:2][CH2:3][N:4]1[C:16]2[CH:15]=[CH:14][C:13]3[C:17](=[O:20])[CH2:18][CH2:19][C:12]=3[C:11]=2[C:10]2[C:9]3[CH2:21][CH2:22][C:23](=[O:24])[C:8]=3[CH:7]=[CH:6][C:5]1=2.[CH3:25][C:26]([CH3:28])=O.C([O-])(O)=O.[Na+].Cl>C(Cl)Cl.CO.O1CCOCC1.C(Cl)(Cl)Cl.CO>[CH:26]([NH:1][CH2:2][CH2:3][N:4]1[C:16]2[CH:15]=[CH:14][C:13]3[C:17](=[O:20])[CH2:18][CH2:19][C:12]=3[C:11]=2[C:10]2[C:9]3[CH2:21][CH2:22][C:23](=[O:24])[C:8]=3[CH:7]=[CH:6][C:5]1=2)([CH3:28])[CH3:25]
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 453811166-(2-aminoethyl)-10,11-dihydro-1H-dicyclopenta[c,g]carbazole-3,9(2H,6H)-dione

生成物 1

HCID 445191266-[2-(isopropylamino)ethyl]-10,11-dihydro-1H-dicyclopenta[c,g]carbazole-3,9(2H,6H)-dione

試薬・触媒・溶媒 4

HCID 887
Methanol
溶媒
2 回
HCID 6344Dichloromethane溶媒3 回
HCID 312751,4-Dioxane溶媒
HCID 21584188Chloroform methanol溶媒

実験手順

Crude compound 59 (1.69 g) was suspended in CH2Cl2 (200 mL). Then acetone (4 mL) and STAB (3.4 g) were added. The mixture was stirred for 24 h (TLC monitoring, eluent: CHCl3-MeOH, 9:1), then poured into an aqueous NaHCO3 solution. Then, another portion of CH2Cl2 and MeOH was added. The organic layer was separated, evaporated, washed with MeCN and ether. Yield of Example 8: 0.759 g. For the preparation of hydrochloride, the isolated product was suspended in a mixture of CH2Cl2 and MeOH, then a solution of HCl in dioxane was added. The resulting mixture was evaporated to dryness, and ethanol was added to the residue. The ethanolic solution was refluxed and cooled, and the precipitate was filtered. Yield of compound Example 8 hydrochloride: 0.684 g. 1H-NMR (DMSO-D6) spectrum: δ 1.24 (6H, d, J=6.6 Hz); 2.77-2.79 (4H, m); 3.34-3.43 (3H, m); 3.81-3.84 (4H, m); 4.91 (2H, t, J=7.3 Hz); 7.83 (2H, d, J=8.6 Hz); 7.91 (2H, d, J=8.6 Hz); 9.11 (2H, br. s). ELSD: 100%, ESI-MS: m/z 360 [M+H].+

後処理

  1. customThe organic layer was separated
  2. customevaporated
  3. washwashed with MeCN and ether
  4. customFor the preparation of hydrochloride
  5. customThe resulting mixture was evaporated to dryness, and ethanol
  6. additionwas added to the residue
  7. temperatureThe ethanolic solution was refluxed
  8. temperaturecooled
  9. filtrationthe precipitate was filtered

出典と根拠

ORDレコード
ord-0a6104f2889d4779992b088f2be66af3
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09108916B2

反応ノート

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