Water → 4-[1-(2-ethoxyethyl)-1H-indol-3-yl]-piperidine-1-carboxylic acid ethyl ester

HRID 227269Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 227269
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][CH:13]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[H-].[Na+].Br[CH2:24][CH2:25][O:26][CH2:27][CH3:28].O>CN(C=O)C>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:24][CH2:25][O:26][CH2:27][CH3:28])[CH:13]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 611412-Bromoethyl ethyl etherHCID 11380267Ethyl 4-(1H-indol-3-yl)piperidine-1-carboxylate

Produkt 1

HCID 114734154-[1-(2-ethoxyethyl)-1H-indol-3-yl]-piperidine-1-carboxylic acid ethyl esterAusbeute 103,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

Under inert atmosphere, a solution of 12.5 g (0.045 mol) of 4-(1H-indol-3-yl)-piperidine-1-carboxylic acid ethyl ester in 50 ml of anhydrous DMF was added dropwise to a suspension containing 2.75 g (0.068 mol) of sodium hydride (60% in mineral oil) in 200 ml of anhydrous DMF. After stirring at room temperature for 1 hour, 6.6 ml (0.06 mol) of 1-bromo-2-ethoxyethane were added. The reaction mixture was heated at 60° C. for 3 hours. The crude mixture was poured into water and extracted with ethyl acetate. After drying, the solvent was removed under reduced pressure and 16 g of a crude oil were obtained and used in the next step without purification.

Aufarbeitung

  1. temperatureThe reaction mixture was heated at 60° C. for 3 hours
  2. extractionextracted with ethyl acetate
  3. customAfter drying
  4. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7b4ac68b3fb341b696e369ba0398ea2a
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560471B2

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