Hydrochloric Acid → 2-(2-Benzo[b]thiophen-5-ylethoxy)-1-piperidino-1-ethanone

HRID 1007925Notes

Reaction equation

HRID 1007925 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([CH2:10][CH2:11][OH:12])[CH:8]=[CH:9][C:2]1=2.[CH3:13][C:14](C)([O-])[CH3:15].[K+].C([O:22][CH2:23][CH3:24])(=O)C.Cl.[CH3:26][N:27]([CH3:30])C=O>O>[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([CH2:10][CH2:11][O:12][CH2:24][C:23]([N:27]3[CH2:30][CH2:15][CH2:14][CH2:13][CH2:26]3)=[O:22])[CH:8]=[CH:9][C:2]1=2

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 119833712-(1-Benzothiophen-5-yl)ethan-1-olHCID 23665647Potassium tert-butoxide

Product 1

HCID 226663742-(2-Benzo[b]thiophen-5-ylethoxy)-1-piperidino-1-ethanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In 28 mL of N,N-dimethylformamide is dissolved 5.60 g of 2-benzo[b]thiophen-5-yl-1-ethanol, to which are added 4.23 g of potassium tert-butoxide and 6.09 g of 1-chloroacetylpiperidine at an ice-cooled temperature. The mixture thus formed is stirred at the same temperature as above for 30 minutes, and then at ambient temperature for 2 hours. The reaction mixture is introduced into a mixture of ethyl acetate and water and adjusted to pH 2.0 with 2 mol/L hydrochloric acid, and then the organic layer is separated. The organic layer is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, the solvent is distilled off under reduced pressure, and the residue is purified by column chromatography (eluent: n-hexane:ethyl acetate=5:1 to 2:1) to obtain 8.50 g of 2-(2-benzo[b]thiophen-5-ylethoxy)-1-piperidino-1-ethanone as an oily product.

Workup

  1. temperaturecooled temperature
  2. customThe mixture thus formed
  3. waitat ambient temperature for 2 hours
  4. customthe organic layer is separated
  5. washThe organic layer is washed with water and saturated aqueous solution of sodium chloride successively
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent is distilled off under reduced pressure
  8. customthe residue is purified by column chromatography (eluent: n-hexane:ethyl acetate=5:1 to 2:1)

Sources & evidence

ORD record
ord-00db6cdc35f4453ba4d7261be6e0f158
Source dataset
uspto-grants-2004_09
Patent number
US06797726B1

Reaction notes

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