Water → N-[2-(2-benzo[b]thiophen-5-ylethoxy)ethyl]-N,N-dipropylamine

HRID 1007893Notes

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]([NH:23][CH2:24][CH2:25][CH3:26])[CH2:21][CH3:22].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][N:23]([CH2:24][CH2:25][CH3:26])[CH2:20][CH2:21][CH3:22])[CH:19]=[CH:18][C:14]1=2

Participants

Conditions

Temperature: 80 °C

Procedure

In 8 mL of N,N-dimethylformamide is dissolved 0.80 g of 2-(2-benzo[b]thiophen-5-ylethoxy)ethyl methanesulfonate, to which are added 0.73 mL of dipropylamine and 0.74 g of potassium carbonate. The resulting mixture is stirred 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 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). Thus, 0.60 of N-[2-(2-benzo[b]thiophen-5-ylethoxy)ethyl]-N,N-dipropylamine is obtained as an oily product.

Workup

customthe organic layer is separated
washThe organic layer is washed with water and saturated aqueous solution of sodium chloride
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=10:1)

Sources & evidence

ORD record: ord-57cac10567b94557a233ed95646d8627
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06797726B1

Reaction notes

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