Hydrochloric Acid → N-[3-(2-benzo[b]thiophen-5-ylethoxy)propyl]-N,N-diethylamine

HRID 1007899

Reaction equation

HRID 1007899 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][C:8]1[CH:16]=[CH:15][C:11]2[S:12][CH:13]=[CH:14][C:10]=2[CH:9]=1.[CH2:17]([NH:19][CH2:20][CH3:21])[CH3:18].O.Cl>CN(C)C=O.C(OCC)(=O)C>[S:12]1[CH:13]=[CH:14][C:10]2[CH:9]=[C:8]([CH2:7][CH2:6][O:5][CH2:4][CH2:3][CH2:2][N:19]([CH2:20][CH3:21])[CH2:17][CH3:18])[CH:16]=[CH:15][C:11]1=2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8021DiethylamineHCID 219900695-[2-(3-Chloropropyloxy)ethyl]benzo[b]thiophene

Product 1

HCID 22666289N-[3-(2-benzo[b]thiophen-5-ylethoxy)propyl]-N,N-diethylamine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

In 6 mL of N,N-dimethylformamide is dissolved 0.80 g of 5-[2-(3-chloropropyloxy)ethyl]benzo[b]-thiophene, to which is added 3.2 mL of diethylamine. The mixture is stirred in an ampoule at 100° C. for 10 hours. After cooling, the reaction mixture is introduced into a mixture of water and ethyl acetate, pH is adjusted to 1.0 with 6 mol/L hydrochloric acid, and the aqueous layer is separated. Ethyl acetate is added to the aqueous layer, pH is adjusted to 10.0 with 5 mol/L aqueous solution of sodium hydroxide, and the organic layer is separated. The organic layer is washed with water and 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 4:1). Thus, 0.48 g of N-[3-(2-benzo[b]thiophen-5-ylethoxy)propyl]-N,N-diethylamine is obtained as an oily product.

Workup

  1. temperatureAfter cooling
  2. customthe aqueous layer is separated
  3. additionEthyl acetate is added to the aqueous layer
  4. customthe organic layer is separated
  5. washThe organic layer is washed with water and 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 4:1)

Sources & evidence

ORD record
ord-4a8da577d4194a3789bebcea626b4cf3
Source dataset
uspto-grants-2004_09
Patent number
US06797726B1

Linked notes

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