Hydrochloric Acid → HCID 22666304, compound

HRID 1007884Notes

Reaction equation

HRID 1007884 reaction equation
[CH2:1]([N:3]([CH2:20][CH3:21])[C:4](=O)[CH2:5][O:6][CH2:7][CH2:8][C:9]1[C:17]([F:18])=[CH:16][C:12]2[S:13][CH:14]=[CH:15][C:11]=2[CH:10]=1)[CH3:2].Cl.O.[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C>[CH2:20]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][O:6][CH2:7][CH2:8][C:9]1[C:17]([F:18])=[CH:16][C:12]2[S:13][CH:14]=[CH:15][C:11]=2[CH:10]=1)[CH3:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 22666443HCID 22666443, compound

Product 1

HCID 22666304HCID 22666304, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

In 20 mL of tetrahydrofuran is dissolved 1.24 g of N,N-diethyl-2-[2-(6-fluorobenzo[b]thiophen-5-yl)ethoxy]-acetamide. The solution is cooled to 5° C., and 7.86 mL of a 1 mol/L solution of borane-tetrahydrofuran complex in tetrahydrofuran is dropwise added thereto. After stirring the resulting mixture at ambient temperature for 2 hours, 4.00 mL of 2 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 13 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=30:1 to 10:1) to obtain 0.90 g of N,N-diethyl-N-{2-[2-(6-fluorobenzo[b]thiophen-5-yl)ethoxy]ethyl}-amine 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=30:1 to 10:1)

Sources & evidence

ORD record
ord-2c4043eaa8d54f7c9abb5f061e76eae2
Source dataset
uspto-grants-2004_09
Patent number
US06797726B1

Reaction notes

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