Hydrochloric Acid → HCID 22666527, compound

HRID 1007906Notes

Reaction equation

HRID 1007906 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH3:22])[C:5](=O)[CH2:6][O:7][CH2:8][CH2:9][C:10]1[C:18]([O:19][CH3:20])=[CH:17][C:13]2[S:14][CH:15]=[CH:16][C:12]=2[CH:11]=1.Cl.O.[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C>[CH3:20][O:19][C:18]1[C:10]([CH2:9][CH2:8][O:7][CH2:6][CH2:5][N:4]([CH3:22])[CH2:3][CH2:2][OH:1])=[CH:11][C:12]2[CH:16]=[CH:15][S:14][C:13]=2[CH:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 68796619HCID 68796619, compound

Product 1

HCID 22666527HCID 22666527, compoundYield 75.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

In 8 mL of tetrahydrofuran is dissolved 0.93 g of N1-(2-hydroxyethyl)-N1-methyl-2-[2-(6-methoxybenzo[b]-thiophen-5-yl)ethoxy]-acetamide. The solution is cooled to 5° C., and 6 mL of 1 mol/L solution of borane-tetrahydrofuran complex in tetrahydrofuran is dropwise added thereto. After stirring the mixture 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 30 minutes. After cooling, water and ethyl acetate are added to the reaction mixture, pH is adjusted to 9.5 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). Thus, 0.67 g of 2-[{2-[2-(6-methoxybenzo[b]thiophen-5-yl)ethoxy]-ethyl}(methyl)amino]-1-ethanol is obtained as an oily product.

Workup

  1. additionis dropwise added
  2. temperaturethe resulting mixture is heated
  3. temperatureunder reflux for 30 minutes
  4. temperatureAfter cooling
  5. customthe organic layer is separated
  6. washThe organic layer is washed with saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent is distilled off under reduced pressure
  9. customthe residue is purified by column chromatography (eluent: chloroform:methanol=10:1 to 5:1)

Sources & evidence

ORD record
ord-9fff2b736d47418b984be199e701191a
Source dataset
uspto-grants-2004_09
Patent number
US06797726B1

Reaction notes

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