Sodium Hydroxide → Diethyl-[4-(1H-indol-5-yloxy)-butyl]-amine

HRID 1633628Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1633628
C(OC([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=O)(C)(C)C.[OH-].[Na+]>CCO>[CH2:25]([N:22]([CH2:23][CH3:24])[CH2:21][CH2:20][CH2:19][CH2:18][O:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[NH:8][CH:9]=[CH:10]2)[CH3:26]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 695488375-(4-Diethylamino-butoxy)-indole-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 18679455Diethyl-[4-(1H-indol-5-yloxy)-butyl]-amineAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

3.9 g (10.8 mmol) 5-(4-Diethylamino-butoxy)-indole-1-carboxylic acid tert-butyl ester in 4 ml EtOH were treated with 0.4 ml halfconc. NaOH at 60° C. for 2 h. The suspension was concentrated in vacuo and the residue dissolved in EtOAc and water. The organic phase was washed with water and dried over Na2SO4. Evaporation yielded 2.7 g (96%) Diethyl-[4-(1H-indol-5-yloxy)-butyl]-amine as brown oil, MS: 261 (MH+).

Aufarbeitung

  1. concentrationThe suspension was concentrated in vacuo
  2. dissolutionthe residue dissolved in EtOAc
  3. washThe organic phase was washed with water
  4. dry with materialdried over Na2SO4
  5. customEvaporation

Quellen und Nachweise

ORD-Eintrag
ord-a70007d2915c45308cae53b33c0735f6
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06503907B2

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