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Dimethylformamide → 1-{4-[(1-Hydroxyethyl)phenethyl]-piperidin-4-yl}-6-acetamidomethylindole

HRID 1790526
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Reaktionsgleichung

Reaktionsgleichung von HRID 1790526
[C:1](=[O:4])([O-])[O-].[K+].[K+].[NH:7]1[CH2:12][CH2:11][CH:10]([N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([CH2:22][NH:23][C:24](=[O:26])[CH3:25])[CH:20]=3)[CH:15]=[CH:14]2)[CH2:9][CH2:8]1.O[CH:28]([C:30]1[CH:38]=[CH:37][C:33](CCBr)=[CH:32][CH:31]=1)[CH3:29].[CH3:39]N(C)C=O>>[OH:4][CH:1]([CH:29]([C:10]1([N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([CH2:22][NH:23][C:24](=[O:26])[CH3:25])[CH:20]=3)[CH:15]=[CH:14]2)[CH2:9][CH2:8][NH:7][CH2:12][CH2:11]1)[CH2:28][C:30]1[CH:38]=[CH:37][CH:33]=[CH:32][CH:31]=1)[CH3:39]
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Komponenten

5

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 220379271-(Piperidin-4-yl)-6-acetamidomethylindoleHCID 220379344-(1-Hydroxyethyl)phenethyl bromide

Produkt 1

HCID 220380321-{4-[(1-Hydroxyethyl)phenethyl]-piperidin-4-yl}-6-acetamidomethylindoleAusbeute 45,3 %

Versuchsvorschrift

Potassium carbonate (0.5 g) was added to a solution of 1-(piperidin-4-yl)-6-acetamidomethylindole (0.10 g) obtained in Example 386-1) and 4-(1-hydroxyethyl)phenethyl bromide (0.07 g) obtained in Production Example 19 in N,N-dimethylformamide (5 ml) and the resultant mixture was stirred at 70° C. for 6 hr. Then the reaction mixtures were concentrated under reduced pressure and the residue was partitioned between chloroform (40 ml) and water (15 ml). The chloroform layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol system) to give the title compound (0.07 g) as a pale yellow wax (yield: 45.3%).

Aufarbeitung

  1. customThen the reaction mixtures
  2. concentrationwere concentrated under reduced pressure
  3. customthe residue was partitioned between chloroform (40 ml) and water (15 ml)
  4. washThe chloroform layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (chloroform/methanol system)

Quellen und Nachweise

ORD-Eintrag
ord-e15c3dfc89994171b108cb79c4a78f5e
Quelldatensatz
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07071201B2

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