Water → Cyclopropyl-{6-[1-(4-fluoro-phenyl)-1h-indol-5-yloxy]-hexyl}-methyl-amine

HRID 1633616Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1633616
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)[CH:13]=[CH:12]2.[H-].[Na+].[CH3:27][CH2:28]OCC.O.[CH3:33][N:34]([CH:36]=O)C>>[CH:36]1([N:34]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH:13]=[CH:12]3)[CH3:33])[CH2:28][CH2:27]1

Komponenten

6

Edukt 5

HCID 962WaterHCID 3283Diethyl EtherHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 117496125-(6-Bromo-hexyloxy)-1-(4-fluoro-phenyl)-1H-indole

Produkt 1

HCID 18679440Cyclopropyl-{6-[1-(4-fluoro-phenyl)-1h-indol-5-yloxy]-hexyl}-methyl-amineAusbeute 73 %

Versuchsvorschrift

195 mg (0.5 mmol) 5-(6-Bromo-hexyloxy)-1-(4-fluoro-phenyl)-1H-indole in 2.5 ml DMF were treated with 185 mg (1 mmol) cyclopropyl-methyl amine·CF3CO2H and 96 mg (2 mmol, 50% in mineral oil) NaH at RT for 2 h and at 60° C. for 3 h. At RT, ether and water were added and the inorganic phase was extracted with ether. The combined organic phases were washed with water, dried over Na2SO4 and evaporated. Purification on silica gel with hexane/ether 1:1 yielded 140 mg (73%) Cyclopropyl-{6-[1-(4-fluoro-phenyl)-1H-indol-5-yloxy]-hexyl}-methyl-amine as light yellow oil, MS: 381 (MH+).

Aufarbeitung

  1. extractionthe inorganic phase was extracted with ether
  2. washThe combined organic phases were washed with water
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customPurification on silica gel with hexane/ether 1:1

Quellen und Nachweise

ORD-Eintrag
ord-938d48b6940f48ac8d2b9d98ce7707bd
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06503907B2

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