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

HRID 1290262

Reaktionsgleichung

Reaktionsgleichung von HRID 1290262
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][CH2:13][C:14](O)=O.O.ON1C2C=CC=CC=2N=N1.C(N=C=NC(C)C)(C)C.Cl.[O:38]1[C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][C:42]=2[O:41][CH2:40][CH:39]1[CH2:48][NH2:49]>CN(C=O)C>[O:38]1[C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][C:42]=2[O:41][CH2:40][CH:39]1[CH2:48][NH:49][CH2:14][CH2:13][CH2:12][CH2:11][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=2)[NH:7][CH:6]=1

Komponenten

6

Edukt 4

HCID 12734DiisopropylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 28498361,4-Benzodioxan, 2-(aminomethyl)-, hydrochlorideHCID 150472684-(5-Fluoro-1H-indol-3-yl)butanoic acid

Produkt 1

HCID 18923897(2,3-Dihydro-benzo[1,4]dioxin-2-ylmethyl)-[4-(5-fluoro-1H-indol-3-yl)-butyl]-amineAusbeute 62,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

5-Fluoroindole-3-butyric acid (1.5 g, 6.8 mmole), 1-hydroxybenzotriazole hydrate (1.1 g, 8.2 mmole) and 1,3-diisopropylcarbodiimide (2.6 ml, 16.3 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 (1.4 g, 6.8 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 of the products were concentrated and washed with a minimum amount of THF to remove a by-product and to give 1.5 g (60%) of the desired product, (2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl)-4-(5-fluoro-1H-indole-3yl)-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 of the products were concentrated
  9. washwashed with a minimum amount of THF
  10. customto remove a by-product

Quellen und Nachweise

ORD-Eintrag
ord-b751c17837eb4944b4c7098d9437aded
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05750724

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