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

HRID 7441Notes

Reaction equation

HRID 7441 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][C:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[S:10][CH:9]=1.FC(F)(F)C(O)=O.[NH:24]1[CH2:27][CH:26]([OH:28])[CH2:25]1.C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O.C(OCC)(=O)C.O>[S:10]1[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:8]([CH2:7][CH2:6][O:5][CH2:4][CH2:3][CH2:2][N:24]2[CH2:27][CH:26]([OH:28])[CH2:25]2)=[CH:9]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 21990109HCID 21990109, compoundHCID 21990122HCID 21990122, compound

Product 1

HCID 235455601-(3-(2-(1-Benzothiophene-3-yl)ethoxy)propyl)-3-azetidinolYield 48.1%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

In 5 mL of dimethyl sulfoxide was dissolved 1.00 g of 3-[2-(3-chloropropoxy)ethyl]-1-benzothiophene, and 1.10 g of 3-azetidinol trifluoroacetate and 1.63 g of potassium carbonate were added to the solution, after which the resulting mixture was stirred at 70° C. for 2 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 10:1) to obtain 0.55 g of 1-{3-[2-(1-benzothiophen-3-yl)ethoxy]propyl}-3-azetidinol as a colorless oil.

Workup

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

Sources & evidence

ORD record
ord-29de0b52a98a445486f5088690f37733
Source dataset
uspto-grants-2006_08
Patent number
US07087594B2

Reaction notes

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