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Indole-3-Butyric Acid → (2,3-Dihydro-benzo[1,4]dioxin-2-ylmethyl)-[4-(1H-indol-3-yl)-butyl]-amine

HRID 1290260
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1290260
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][CH2:12][C:13](O)=O)=[CH:2]1.O.ON1C2C=CC=CC=2N=N1.C(N=C=NC(C)C)(C)C.Cl.[O:37]1[C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=2[O:40][CH2:39][CH:38]1[CH2:47][NH2:48]>CN(C=O)C>[O:37]1[C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=2[O:40][CH2:39][CH:38]1[CH2:47][NH:48][CH2:13][CH2:12][CH2:11][CH2:10][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8617Indole-3-Butyric AcidHCID 12734DiisopropylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 28498361,4-Benzodioxan, 2-(aminomethyl)-, hydrochloride

Produkt 1

HCID 18923886(2,3-Dihydro-benzo[1,4]dioxin-2-ylmethyl)-[4-(1H-indol-3-yl)-butyl]-amineAusbeute 59,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

3-Indolebutyric acid (1.2 g, 6.0 mmole), 1-hydroxybenzotriazole hydrate (0.97 g, 7.2 mmole) and 1,3-diisopropylcarbodiimide (2.3 ml, 14.4 mmole) were combined in 100 ml of DMF and stirred at room temperature for 2 hours under a nitrogen atmosphere. To this was added dropwise 2,3-dihydro-1,4-benzodioxin-2methanamine hydrochloride (1.2 g, 6.0 mmole) in 50 ml of DMF and the mixture was further stirred for 24 hours. The solvent was removed and the residue partitioned between dichloromethane and water. The separated dichloromethane layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. The residue was chromatographed on a silica gel column using ethyl acetate as the eluant. Fractions were concentrated and washed with a minimum amount of THF to remove a by-product and to give 1.2 g (57%) of the desired product, (2,3-dihydro-benzo [1,4]dioxin-2-ylmethyl)-4-(1H-indol-3-yl)-butanamide, as an oil.

Aufarbeitung

  1. stirringthe mixture was further stirred for 24 hours
  2. customThe solvent was removed
  3. customthe residue partitioned between dichloromethane and water
  4. dry with materialThe separated dichloromethane layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customThe residue was chromatographed on a silica gel column
  8. concentrationFractions were concentrated
  9. washwashed with a minimum amount of THF
  10. customto remove a by-product

Quellen und Nachweise

ORD-Eintrag
ord-6126f80f08954d2a87a485f198927309
Quelldatensatz
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05750724

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