Water → 1-(3-(2-(1-Benzothiophene-5-yl)ethoxy)propyl)-3-pyrrolidinol

HRID 597820

Reaktionsgleichung

Reaktionsgleichung von HRID 597820
Cl[CH2:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]2[S:15][CH:14]=[CH:13][C:12]=2[CH:16]=1.[NH:17]1[CH2:21][CH2:20][CH:19]([OH:22])[CH2:18]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.C(OCC)(=O)C>[S:15]1[C:11]2[CH:10]=[CH:9][C:8]([CH2:7][CH2:6][O:5][CH2:4][CH2:3][CH2:2][N:17]3[CH2:21][CH2:20][CH:19]([OH:22])[CH2:18]3)=[CH:16][C:12]=2[CH:13]=[CH:14]1

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 982104-HydroxypyrrolidineHCID 219900695-[2-(3-Chloropropyloxy)ethyl]benzo[b]thiophene

Produkt 1

HCID 219900371-(3-(2-(1-Benzothiophene-5-yl)ethoxy)propyl)-3-pyrrolidinolAusbeute 54,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

1.20 g of 5-(2-(3-chloropropoxy)ethyl)-1-benzothiophene was dissolved in 12 ml of N,N-dimethylformamide. Thereafter, 0.82 g of 3-pyrrolidinol and 1.30 g of potassium carbonate were added to the obtained solution, and the mixture was then stirred at 85° C. for 2.5 hours. After the reaction mixture was cooled, water and ethyl acetate were added thereto, and an organic layer was separated. The organic layer was successively washed with water and a saturated saline solution, and then dried over anhydrous magnesium sulfate. Thereafter, the solvent was distilled away under a reduced pressure. The residue was purified by column chromatography (eluent; chloroform:methanol=20:1 to 10:1), so as to obtain 0.78 g of an achromatic oil product, 1-(3-(2-(1-benzothiophene-5-yl)ethoxy)propyl)-3-pyrrolidinol.

Aufarbeitung

  1. temperatureAfter the reaction mixture was cooled
  2. customan organic layer was separated
  3. washThe organic layer was successively washed with water
  4. dry with materiala saturated saline solution, and then dried over anhydrous magnesium sulfate
  5. distillationThereafter, the solvent was distilled away under a reduced pressure
  6. customThe residue was purified by column chromatography (eluent; chloroform:methanol=20:1 to 10:1)

Quellen und Nachweise

ORD-Eintrag
ord-d8bbc063d5a14a22b31ca1bada1a2617
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897594B2

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