Sodium Iodide → 6-[6-(4-hydroxypiperidinyl)hexoxy]-3-methoxy-4H-1-benzopyran-4-one

HRID 1708726Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1708726
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]2[O:17][CH:16]=[C:15]([O:18][CH3:19])[C:14](=[O:20])[C:13]=2[CH:21]=1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].[OH:30][CH:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1>CC(=O)CC>[OH:30][CH:31]1[CH2:36][CH2:35][N:34]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]3[O:17][CH:16]=[C:15]([O:18][CH3:19])[C:14](=[O:20])[C:13]=3[CH:21]=2)[CH2:33][CH2:32]1

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 79341Piperidin-4-olHCID 189596986-(6-chlorohexoxy)-3-methoxy-4H-1-benzopyran-4-one

Produkt 1

HCID 189597226-[6-(4-hydroxypiperidinyl)hexoxy]-3-methoxy-4H-1-benzopyran-4-oneAusbeute 82,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

A mixture of 2 g of 6-(6-chlorohexoxy)-3-methoxy-4H-1-benzopyran-4-one, 1 g of sodium iodide, 0.6 g of potassium carbonate, and 1.4 g of 4-hydroxypiperidine was refluxed in butanone for 96 hours. The solvent was removed and the residue stirred with ethyl acetate and filtered. The solution was washed with water and then dried over sodium sulfate. The solvent was removed to give an oil which was chromatographed over silica gel to give 2 g of 6-[6-(4-hydroxypiperidinyl)hexoxy]-3-methoxy-4H-1-benzopyran-4-one which was converted to the hydrochloride salt by dissolving in ethyl acetate and adding 1 N ethereal HCL: mp 124°-125° C.

Aufarbeitung

  1. customThe solvent was removed
  2. filtrationfiltered
  3. washThe solution was washed with water
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed
  6. customto give an oil which
  7. customwas chromatographed over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-a3340a678afa462e8e8b70bcef5e8e5c
Quelldatensatz
uspto-grants-1994_10
Patentnummer
US05359098

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