Sodium Iodide → HCID 19778675, Verbindung

HRID 2082459

Reaktionsgleichung

Reaktionsgleichung von HRID 2082459
[CH2:1]([O:8][C:9]1[CH:20]=[CH:19][C:12]2[O:13][CH:14]([CH2:17][NH2:18])[CH2:15][O:16][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:22][CH2:23][CH2:24][O:25][C:26]1[CH:35]=[C:34]2[C:29]([CH:30]=[CH:31][C:32](=[O:36])[O:33]2)=[CH:28][CH:27]=1.C(N(C(C)C)CC)(C)C.[I-].[Na+]>CN(C=O)C>[C:2]1([CH2:1][O:8][C:9]2[CH:20]=[CH:19][C:12]3[O:13][CH:14]([CH2:17][NH:18][CH2:22][CH2:23][CH2:24][O:25][C:26]4[CH:27]=[CH:28][C:29]5[CH:30]=[CH:31][C:32](=[O:36])[O:33][C:34]=5[CH:35]=4)[CH2:15][O:16][C:11]=3[CH:10]=2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 19006662H-1-Benzopyran-2-one, 7-(3-chloropropoxy)-HCID 197786802,3-Dihydro-6-benzyloxy-1,4-benzodioxin-2-methanamine

Produkt 1

HCID 19778675HCID 19778675, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
108 °C

Versuchsvorschrift

2,3-Dihydro-6-benzyloxy-1,4-benzodioxin-2-methanamine (2.4 g, 8.85 mmole), 7-(3-chloropropoxy)coumarin (2.15 g, 9.0 mmole), diisopropylethylamine (7.0 ml, 40.2 mmole) and sodium iodide (1.35 g, 9.0 mmole) were combined in 200 ml of DMF and heated at 108° C. for 2 days under a nitrogen atmosphere. The solvent was then removed and replaced with dichloromethane. The mixture was washed with an equal volume of water dried over magnesium sulfate, filtered, and concentrated in vacuum. The residue was column chromatographed on silica gel using 1% methanol/dichloromethane as eluant. The product-containing fractions (Rf=0.27 on silica gel tlc with 2.5% methanol/dichloromethane) were combined and concentrated in vacuum and the residue redissolved in dichloromethane and boiled on a hot plate, the solvent gradually being replaced with isopropanol. Upon addition of 6 ml of 4N HCl/isopropanol and cooling, 1.22 g of the title compound, m.p. 184°-187° C., precipitated as a beige solid, monohydrochloride.

Aufarbeitung

  1. customThe solvent was then removed
  2. washThe mixture was washed with an equal volume of water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum
  6. customchromatographed on silica gel using 1% methanol/dichloromethane as eluant
  7. concentrationconcentrated in vacuum
  8. dissolutionthe residue redissolved in dichloromethane
  9. additionUpon addition of 6 ml of 4N HCl/isopropanol
  10. temperaturecooling
  11. custom1.22 g of the title compound, m.p. 184°-187° C., precipitated as a beige solid, monohydrochloride

Quellen und Nachweise

ORD-Eintrag
ord-0d1e7fe96ba2490e871d6f69400b2fa7
Quelldatensatz
uspto-grants-1993_02
Patentnummer
US05189171

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