Hydrochloric Acid → HCID 22666333, compound

HRID 1007911Notes

Reaction equation

HRID 1007911 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH3:21])[C:5](=O)[CH2:6][O:7][CH2:8][CH2:9][C:10]1[CH:19]=[CH:18][C:13]2[S:14][C:15]([F:17])=[CH:16][C:12]=2[CH:11]=1.Cl.O.[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C>[F:17][C:15]1[S:14][C:13]2[CH:18]=[CH:19][C:10]([CH2:9][CH2:8][O:7][CH2:6][CH2:5][N:4]([CH3:21])[CH2:3][CH2:2][OH:1])=[CH:11][C:12]=2[CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 68800171HCID 68800171, compound

Product 1

HCID 22666333HCID 22666333, compoundYield 86.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

In 7 mL of tetrahydrofuran is dissolved 0.70 g of N1-(2-hydroxyethyl)-N1-methyl-2-[2-(2-fluorobenzo[b]thiophen-5-yl)ethoxy]-acetamide. The solution is cooled to 5° C., to which is dropwise added 6.7 mL of 1 mol/L solution of borane-tetrahydrofuran complex in tetrahydrofuran. The resulting mixture is stirred at ambient temperature overnight, 1.5 mL of 6 mol/L hydrochloric acid is dropwise added, and the resulting mixture is heated under reflux for one hour. After cooling, water and ethyl acetate are added to the reaction mixture, pH is adjusted to 10.5 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 5:1) to obtain 0.58 g of 2-[{2-[2-(2-fluorobenzo[b]thiophen-5-yl)ethoxy]ethyl}(methyl)amino]-1-ethanol as an oily product.

Workup

  1. temperaturethe resulting mixture is heated
  2. temperatureunder reflux for one hour
  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 to 5:1)

Sources & evidence

ORD record
ord-f2c330089de84809823baf0a909ab8da
Source dataset
uspto-grants-2004_09
Patent number
US06797726B1

Reaction notes

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