Hydrochloric Acid → 2-[[2-(2-Benzo[b]thiophen-5-ylethoxy)ethyl](methyl)amino]-1-propanol

HRID 1007915Notes

Reaction equation

HRID 1007915 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([CH2:10][CH2:11][O:12][CH2:13][CH2:14][N:15]([CH:18]([CH3:21])[CH2:19][OH:20])[CH:16]=O)[CH:8]=[CH:9][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]=[C:7]([CH2:10][CH2:11][O:12][CH2:13][CH2:14][N:15]([CH3:16])[CH:18]([CH3:21])[CH2:19][OH:20])[CH:8]=[CH:9][C:2]1=2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 22666440N-[2-(2-benzo[b]thiophen-5-ylethoxy)ethyl]-N-(2-hydroxy-1-methylethyl)-formamide

Product 1

HCID 226662802-[[2-(2-Benzo[b]thiophen-5-ylethoxy)ethyl](methyl)amino]-1-propanolYield 48.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

In 4.3 mL of tetrahydrofuran is dissolved 0.43 g of N-[2-(2-benzo[b]thiophen-5-ylethoxy)ethyl]-N-(2-hydroxy-1-methylethyl)-formamide. To the solution thus obtained is dropwise added at an ice-cooled temperature 5.60 mL of 1 mol/L solution of borane-tetrahydrofuran complex in tetrahydrofuran. The resulting mixture is stirred at ambient temperature for 1.5 hours. The reaction mixture is acidified with 1.9 mL of 6 mol/L hydrochloric acid and heated under reflux for one hour. After cooling the reaction mixture to ambient temperature, water and ethyl acetate are added, pH is adjusted to 9.5 with 2 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 oily product thus obtained is purified by column chromatography (eluent: chloroform:methanol=30:1) to obtain 0.20 g of 2-[[2-(2-benzo[b]thiophen-5-ylethoxy)ethyl](methyl)amino]-1-propanol as a light yellow-colored oily product.

Workup

  1. customTo the solution thus obtained
  2. temperatureheated
  3. temperatureunder reflux for one hour
  4. temperatureAfter cooling the reaction mixture to ambient temperature
  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 oily product thus obtained
  10. customis purified by column chromatography (eluent: chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-4958d14939d843e4b5e7686f39325f47
Source dataset
uspto-grants-2004_09
Patent number
US06797726B1

Reaction notes

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