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Diisopropylcarbodiimide → (2,3-Dihydro-benzo[1,4]dioxin-2-ylmethyl)-[4-(5-methoxy-1H-indol-3-yl)-butyl]-amine

HRID 1290266
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1290266
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][CH2:14][C:15](O)=O.O.ON1C2C=CC=CC=2N=N1.C(N=C=NC(C)C)(C)C.Cl.[O:39]1[C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=2[O:42][CH2:41][CH:40]1[CH2:49][NH2:50]>CN(C=O)C>[O:39]1[C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=2[O:42][CH2:41][CH:40]1[CH2:49][NH:50][CH2:15][CH2:14][CH2:13][CH2:12][C:6]1[C:5]2[C:9](=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=2)[NH:8][CH:7]=1
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Komponenten

6

Edukt 4

HCID 12734DiisopropylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 28498361,4-Benzodioxan, 2-(aminomethyl)-, hydrochlorideHCID 112417775-Methoxyindole-3-butyric acid

Produkt 1

HCID 18923900(2,3-Dihydro-benzo[1,4]dioxin-2-ylmethyl)-[4-(5-methoxy-1H-indol-3-yl)-butyl]-amineAusbeute 76,7 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

5-methoxyindole-3-butyric acid (1.5 g, 6.4 mmole), 1-hydroxybenzotriazole hydrate (1.0 g, 7.7 mmole) and 1,3-diisopropylcarbodiimide (2.4 ml, 15.4 mmole) were combined in 150 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-2-methanamine hydrochloride (1.3 g, 6.4 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 containing product were concentrated and washed with a minimum amount of TBF to remove a by-product and to give 1.8 g (74%) of the desired product, (2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl)-4-(5-1H-indole-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. additionFractions containing product
  9. concentrationwere concentrated
  10. washwashed with a minimum amount of TBF
  11. customto remove a by-product

Quellen und Nachweise

ORD-Eintrag
ord-69eabdf1c20d4ce088acdcf841e1a851
Quelldatensatz
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05750724

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