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Ethanol → HCID 18706963, Verbindung

HRID 1422084
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1422084
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH2:9]([O:16][C:17]1[C:18]2[N:19]3[C:23](=[CH:24][CH:25]=1)[C:22]([CH2:26][CH3:27])=[C:21]([C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[CH:30][CH:29]=1)[C:20]3=[C:42]([CH2:44][O:45][CH2:46][CH2:47][CH2:48][CH2:49]Cl)[CH:43]=2)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(O)C>CN(C)C=O.O>[CH2:9]([O:16][C:17]1[C:18]2[N:19]3[C:23](=[CH:24][CH:25]=1)[C:22]([CH2:26][CH3:27])=[C:21]([C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[CH:30][CH:29]=1)[C:20]3=[C:42]([CH2:44][O:45][CH2:46][CH2:47][CH2:48][CH2:49][N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[CH:43]=2)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 702EthanolHCID 8082PiperidineHCID 24758Sodium hydrideHCID 187069385-Benzyloxy-2-(4-benzyloxyphenyl)-3-((4-chlorobutoxy)methyl)-1-ethylpyrrolo[2,1,5-cd]indolizine

Produkt 1

HCID 18706963HCID 18706963, VerbindungAusbeute 5,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Piperidine (0.104 g, 1.22 mmol) was dissolved in 50 ml of dry dimethylformamide under a nitrogen atmosphere and sodium hydride (60% in oil) 47 mg, 1.16 mmol) was added. The mixture was stirred for 1/2 hour. 5-Benzyloxy-2-(4-benzyloxyphenyl)-3-((4-chlorobutoxy)methyl)-1-ethylpyrrolo[2,1,5-cd]indolizine (0.337 g, 0.583 mmol) was added and the mixture was stirred at 55-65° for 7 days. Ethanol (10 ml) was added dropwise, and the reaction mxiture was diluted with 250 ml of water. The organic material was extracted into ethyl acetate (3×100 ml), and the combined organic layers were washed with brine and dried over sodium sulfate. The solvent was eaporated and the crude product was purified by column chromatography over silica gel 60, using 5% of methanol in dichloromethane as the eluent. Fractions containing the product were collected to afford 21 mg (5%) of 5-benzyloxy-2-(4-benzyloxyphenyl)-1-ethyl-3-((4-piperidinobutoxy)methyl)pyrrolo[2,1,5-cd ]indolizine as an oil. MS(SP): m/z 640 (M+). 1H-NMR (DMSO-d6, 300 MHz) δ: 1.28-1.58 (m, 13H); 2.21-2.57 (m, 6H); 3.08 (q, 2H); 3.37-3.48 (m, 2H+H2O); 4.72 (s, 2H); 5.20 (s, 2H); 5.60 (s, 2H); 7.22 (d, 2H); 7.32-7.69 (m, 14H); 7.98 (d, 1H).

Aufarbeitung

  1. stirringthe mixture was stirred at 55-65° for 7 days
  2. extractionThe organic material was extracted into ethyl acetate (3×100 ml)
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. customthe crude product was purified by column chromatography over silica gel 60
  6. additionFractions containing the product
  7. customwere collected

Quellen und Nachweise

ORD-Eintrag
ord-dc0a4c68725a4089aae905b26a7e5bf5
Quelldatensatz
uspto-grants-2000_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06080754

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