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

HRID 1007933Notes

Reaction equation

CS(O[CH2:6][CH2:7][O:8][CH2:9][CH2:10][C:11]1[CH:19]=[CH:18][C:14]2[S:15][CH:16]=[CH:17][C:13]=2[CH:12]=1)(=O)=O.[CH2:20]([NH2:23])[C:21]#[CH:22].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.C(OCC)(=O)C>[S:15]1[CH:16]=[CH:17][C:13]2[CH:12]=[C:11]([CH2:10][CH2:9][O:8][CH2:7][CH2:6][NH:23][CH2:20][C:21]#[CH:22])[CH:19]=[CH:18][C:14]1=2

Participants

Conditions

Temperature: 80 °C

Procedure

In 15 mL of N,N-dimethylformamide is dissolved 3.00 g of 2-(2-benzo[b]thiophen-5-ylethoxy)-ethyl methanesulfonate, to which are added 1.40 mL of propargylamine and 2.76 g of potassium carbonate. The mixture is heated at 80° C. for 3 hours. The reaction mixture is introduced into a mixture of water and ethyl acetate, 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, the solvent is distilled off under reduced pressure, and the residue is purified by column chromatography (eluent: chloroform:methanol=30:1 to 20:1) to obtain 1.63 g of N-[2-(2-benzo[b]thiophen-5-ylethoxy)ethyl]-N-(2-propynyl)amine as an oily product.

Workup

customthe organic layer is separated
washThe organic layer is washed with water and saturated aqueous solution of sodium chloride successively
dry with materialdried over anhydrous magnesium sulfate
distillationthe solvent is distilled off under reduced pressure
customthe residue is purified by column chromatography (eluent: chloroform:methanol=30:1 to 20:1)

Sources & evidence

ORD record: ord-b4c0ac5b5c144bd4afa623bb7a232fb6
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06797726B1

Reaction notes

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