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

HRID 597811Notes

Reaction equation

HRID 597811 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

1.00 g of 3-(2-(3-chloropropoxy)ethyl)-1-benzothiophene was dissolved in 5 ml of dimethyl sulfoxide. Thereafter, 1.10 g of 3-azetidinol trifluoroacetate and 1.63 g of potassium carbonate were added to the obtained solution, and the mixture was then stirred at 70° C. for 2 hours. After cooling, water and ethyl acetate were added to the reaction mixture. The pH of the mixture was adjusted to pH 1 by addition of 6 mol/l hydrochloric acid, and a water layer was then separated. Ethyl acetate was added to the water layer, and the pH of the obtained mixture was adjusted to pH 10 by addition of a 2 mol/l aqueous sodium hydroxide solution, followed by separation of an organic layer. 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=30:1 to 10:1), so as to obtain 0.55 g of an achromatic oil product, 1-(3-(2-(1-benzothiophene-3-yl)ethoxy)propyl)-3-azetidinol.

Workup

  1. temperatureAfter cooling
  2. customa water layer was then separated
  3. additionEthyl acetate was added to the water layer
  4. additionthe pH of the obtained mixture was adjusted to pH 10 by addition of a 2 mol/l aqueous sodium hydroxide solution
  5. customfollowed by separation of an organic layer
  6. washThe organic layer was successively washed with water
  7. dry with materiala saturated saline solution, and then dried over anhydrous magnesium sulfate
  8. distillationThereafter, the solvent was distilled away under a reduced pressure
  9. customThe residue was purified by column chromatography (eluent; chloroform:methanol=30:1 to 10:1)

Sources & evidence

ORD record
ord-9bb29b7991a64b35871c741ce5ae4bd6
Source dataset
uspto-grants-2011_03
Patent number
US07897594B2

Reaction notes

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