Hydrochloric Acid → 1-(3-(2-(1-Benzothiophene-6-yl)ethoxy)propyl)-3-azetidinol

HRID 7438

Reaktionsgleichung

Reaktionsgleichung von HRID 7438
Cl[CH2:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][C:8]1[CH:16]=[CH:15][C:11]2[CH:12]=[CH:13][S:14][C:10]=2[CH:9]=1.Cl.[NH:18]1[CH2:21][CH:20]([OH:22])[CH2:19]1.C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O.C(OCC)(=O)C.O>[S:14]1[C:10]2[CH:9]=[C:8]([CH2:7][CH2:6][O:5][CH2:4][CH2:3][CH2:2][N:18]3[CH2:21][CH:20]([OH:22])[CH2:19]3)[CH:16]=[CH:15][C:11]=2[CH:12]=[CH:13]1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 27592903-Hydroxyazetidine hydrochlorideHCID 219900846-(2-(3-Chloropropoxy)ethyl)-1-benzothiophene

Produkt 1

HCID 235455641-(3-(2-(1-Benzothiophene-6-yl)ethoxy)propyl)-3-azetidinolAusbeute 24,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

In 5 mL of dimethyl sulfoxide was dissolved 1.00 g of 6-[2-(3-chloropropoxy)ethyl]-1-benzothiophene, and 0.86 g of 3-azetidinol hydrochloride and 1.63 g of potassium carbonate were added to the solution. The resulting mixture was stirred at 75° C. for 2.5 hours and then at 95° C. for 1.5 hours. After the reaction mixture was cooled, water and ethyl acetate were added thereto and the pH was adjusted to 1 with 6 mol/L hydrochloric acid, and the aqueous layer was separated. Ethyl acetate was added to the aqueous layer and the. pH was adjusted to 10 with a 2 mol/L aqueous sodium hydroxide solution, after which the organic layer was separated. The organic layer was washed with water and then a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then distilled under reduced pressure to remove the solvent. The residue was purified by a column chromatography (eluent; chloroform:methanol=30:1 to 5:1) to obtain 0.28 g of 1-{3-[2-(1-benzothiophen-6-yl)ethoxy]propyl}-3-azetidinol as a colorless oil.

Aufarbeitung

  1. additionwere added to the solution
  2. waitat 95° C. for 1.5 hours
  3. temperatureAfter the reaction mixture was cooled
  4. customthe aqueous layer was separated
  5. additionEthyl acetate was added to the aqueous layer
  6. customafter which the organic layer was separated
  7. washThe organic layer was washed with water
  8. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  9. distillationdistilled under reduced pressure
  10. customto remove the solvent
  11. customThe residue was purified by a column chromatography (eluent; chloroform:methanol=30:1 to 5:1)

Quellen und Nachweise

ORD-Eintrag
ord-5c37f61942b04b9e986f75c9bbc72dab
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087594B2

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