Hydrochloric Acid → Edonerpic

HRID 1092763Notes

Reaction equation

HRID 1092763 reaction equation
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.Cl.[NH:18]1[CH2:21][CH:20]([OH:22])[CH2:19]1.[OH-].[Na+].Cl>CS(C)=O.C(OCC)(=O)C.O>[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:18]3[CH2:21][CH:20]([OH:22])[CH2:19]3)=[CH:16][C:12]=2[CH:13]=[CH:14]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 27592903-Hydroxyazetidine hydrochlorideHCID 219900695-[2-(3-Chloropropyloxy)ethyl]benzo[b]thiophene

Product 1

HCID 9901946EdonerpicYield 64.2%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

In 30 mL of dimethyl sulfoxide was dissolved 6.50 g of 5-[2-(3-chloropropoxy)ethyl]-1-benzothiophene, and to the solution were added 5.60 g of 3-azetidinol hydrochloride and 15.3 mL of a 5 mol/L aqueous sodium hydroxide solution, after which the resulting mixture was stirred at 65° C. for 3.5 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 5 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 4.77 g of 1-{3-[2-(1-benzothiophen-5-yl)ethoxy]propyl}-3-azetidinol.

Workup

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

Sources & evidence

ORD record
ord-b5670f55af934e2abce2b66f83c7ab63
Source dataset
uspto-grants-2012_03
Patent number
US08129535B2

Reaction notes

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