Hydrochloric Acid → HCID 22666326, compound

HRID 1007903Notes

Reaction equation

HRID 1007903 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[CH:7][CH:8]=[C:9]([CH2:10][CH2:11][O:12][CH2:13][C:14]([N:16]([CH2:19][CH3:20])[CH2:17][CH3:18])=O)[C:2]1=2.Cl.O.[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C>[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[CH:7][CH:8]=[C:9]([CH2:10][CH2:11][O:12][CH2:13][CH2:14][N:16]([CH2:17][CH3:18])[CH2:19][CH3:20])[C:2]1=2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 22666556HCID 22666556, compound

Product 1

HCID 22666326HCID 22666326, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

In 14 mL of tetrahydrofuran is dissolved 1.36 g of 2-(2-benzo[b]thiophen-7-ylethoxy)-N,N-diethylacetamide. The solution is cooled to 5° C., and 14 mL of 1 mol/L solution of borane-tetrahydrofuran complex in tetrahydrofuran is dropwise added thereto. The resulting mixture is stirred at ambient temperature overnight, and then 5.00 mL of 6 mol/L hydrochloric acid is dropwise added, and the resulting mixture is heated under reflux for 30 minutes. After cooling, water and ethyl acetate are added to the reaction mixture, pH is adjusted to 9 with 5 mol/L aqueous solution of sodium hydroxide, and the organic layer is separated. The organic layer is washed with saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, the solvent is distilled off under reduced pressure, and the residue is purified by column chromatography (eluent: chloroform:methanol=10:1) to obtain 1.10 g of N-[2-(2-benzo[b]thiophen-7-ylethoxy)ethyl]-N,N-diethylamine as an oily product.

Workup

  1. temperaturethe resulting mixture is heated
  2. temperatureunder reflux for 30 minutes
  3. temperatureAfter cooling
  4. customthe organic layer is separated
  5. washThe organic layer is washed with saturated aqueous solution of sodium chloride
  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: chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-2c5f6ce2ddb144f7bac3ca96b6498983
Source dataset
uspto-grants-2004_09
Patent number
US06797726B1

Reaction notes

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