Water → N-[2-(2-benzo[b]thiophen-5-ylethoxy)ethyl]-N-benzyl-N-(2-propynyl)amine

HRID 1007917Notes

Reaction equation

HRID 1007917 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][NH:15][CH2:16][C:17]#[CH:18])[CH:8]=[CH:9][C:2]1=2.[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.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]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:16][C:17]#[CH:18])[CH:8]=[CH:9][C:2]1=2

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 22666513N-[2-(2-benzo[b]thiophen-5-ylethoxy)ethyl]-N-(2-propynyl)amine

Product 1

HCID 22666539N-[2-(2-benzo[b]thiophen-5-ylethoxy)ethyl]-N-benzyl-N-(2-propynyl)amineYield 82.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 3 ml of N,N-dimethylformamide is dissolved 0.60 g of N-[2-(2-benzo[b]thiophen-5-ylethoxy)ethyl]-N-(2-propynyl)amine, to which are added 0.40 g of benzyl bromide and 0.35 g of potassium carbonate. The mixture is stirred at ambient temperature for one hour. Water and ethyl acetate are added to the reaction mixture, and the organic layer is separated. The organic layer is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. The residue is purified by column chromatography (eluent: chloroform:methanol=10:1 to 7:1) to obtain 0.67 g of N-[2-(2-benzo[b]thiophen-5-ylethoxy)ethyl]-N-benzyl-N-(2-propynyl)amine as an oily product.

Workup

  1. customthe organic layer is separated
  2. washThe organic layer is washed with water and saturated aqueous solution of sodium chloride successively
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent is distilled off under reduced pressure
  5. customThe residue is purified by column chromatography (eluent: chloroform:methanol=10:1 to 7:1)

Sources & evidence

ORD record
ord-4df137d659d3485ba32380ff5c03b383
Source dataset
uspto-grants-2004_09
Patent number
US06797726B1

Reaction notes

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