Water → N-(1-{3-[2-(1-benzothiophen-5-yl)ethoxy]propyl}-3-azetidinyl)acetamide

HRID 597812

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]2[S:15][CH:14]=[CH:13][C:12]=2[CH:16]=1.[NH:17]1[CH2:20][CH:19]([NH:21][C:22](=[O:24])[CH3:23])[CH2:18]1.O.C(OCC)(=O)C>CN(C)C=O>[S:15]1[C:11]2[CH:10]=[CH:9][C:8]([CH2:7][CH2:6][O:5][CH2:4][CH2:3][CH2:2][N:17]3[CH2:20][CH:19]([NH:21][C:22](=[O:24])[CH3:23])[CH2:18]3)=[CH:16][C:12]=2[CH:13]=[CH:14]1

Participants

Conditions

Temperature: 90 °C

Procedure

0.80 g of 5-(2-(3-chloropropoxy)ethyl)-1-benzothiophene was dissolved in 8 ml of N,N-dimethylformamide. Thereafter, 1.20 g of N-(3-azetidinyl)acetamide was added to the obtained solution, and the obtained mixture was stirred at 90° C. for 12 hours. After cooling, water and ethyl acetate were added to the reaction mixture, and an organic layer was separated. The organic layer was successively washed with water and a saturated saline solution, and then dried over anhydrous magnesium sulfate. Thereafter, the solvent was distilled away under a reduced pressure. The residue was purified by column chromatography (eluent; chloroform:methanol=7:1), so as to obtain 0.39 g of a light yellow oil product, N-(1-(3-(2-(1-benzothiophene-5-yl)ethoxy)propyl)-3-azetidinyl)acetamide.

Workup

temperatureAfter cooling
customan organic layer was separated
washThe organic layer was successively washed with water
dry with materiala saturated saline solution, and then dried over anhydrous magnesium sulfate
distillationThereafter, the solvent was distilled away under a reduced pressure
customThe residue was purified by column chromatography (eluent; chloroform:methanol=7:1)

Sources & evidence

ORD record: ord-996ee61b18a94877a3d1ccc2f71f8f95
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897594B2

Linked notes

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