Sodium hydride → 1-(8-Hydroxyoctyl)-2-(3-pyridyl)-3-methylindole

HRID 1633131

Reaktionsgleichung

Reaktionsgleichung von HRID 1633131
[H-].[Na+].[CH3:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]=1[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1.O1CCCCC1[O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]Br>CN(C)C=O>[OH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][N:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4]([CH3:3])=[C:5]1[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 1709162H-Pyran, 2-[(8-bromooctyl)oxy]tetrahydro-HCID 155913683-Methyl-2-(3-pyridyl)indole

Produkt 1

HCID 204416611-(8-Hydroxyoctyl)-2-(3-pyridyl)-3-methylindole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

To a suspension of 2.9 g (0.06 mole) of 50% sodium hydride in mineral oil in 40 ml of dimethylformamide under nitrogen at 0°-5° is added dropwise over 20 minutes a solution of 10.4 g of 3-methyl-2-(3-pyridyl)indole in 60 ml of dimethylformamide. The mixture is stirred for 0.5 hour at 0°-5° followed by the dropwise addition of 17.6 g (0.06 mole) of 1-tetrahydropyranyloxy-8-bromooctane in 50 ml of dimethylformamide. After stirring at 0°-10° for 1 hour and at room temperature for 0.5 hour, the reaction mixture is poured into ice-water and extracted with ether. The ether extract is washed with water, dried over MgSO4 and evaporated to dryness. The residue is dissolved in 100 ml of 3N hydrochloric acid, the resulting mixture is kept at room temperature for 0.5 hour, washed with ether, basified with aqueous with 3N sodium hydroxide solution and extracted with methylene chloride. The methylene chloride solution is evaporated to dryness to give 1-(8-hydroxyoctyl)-2-(3-pyridyl)-3-methylindole.

Aufarbeitung

  1. stirringAfter stirring at 0°-10° for 1 hour and at room temperature for 0.5 hour
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. washis washed with water
  5. dry with materialdried over MgSO4
  6. customevaporated to dryness
  7. dissolutionThe residue is dissolved in 100 ml of 3N hydrochloric acid
  8. waitthe resulting mixture is kept at room temperature for 0.5 hour
  9. washwashed with ether
  10. extractionextracted with methylene chloride
  11. customThe methylene chloride solution is evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-486f99ae28c54cac87d1b923e76288b0
Quelldatensatz
uspto-grants-1984_10
Patentnummer
US04478842

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