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

HRID 1092765

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

In 8 mL of N,N-dimethylformamide was dissolved 0.80 g of 5-[2-(3-chloropropoxy)ethyl]-1-benzothiophene, and 1.20 g of N-(3-azetidinyl)acetamide was added to the solution, after which the resulting mixture was stirred at 90° C. for 12 hours. After the reaction mixture was cooled, water and ethyl acetate were added thereto and the organic layer was separated. The organic layer was washed with water and then a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then distilled under reduced pressure to remove the solvent. The residue was purified by a column chromatography (eluent; chloroform:methanol=7:1) to obtain 0.39 g of N-(1-{3-[2-(1-benzothiophen-5-yl)ethoxy]propyl}-3-azetidinyl)acetamide as a light-yellow oil.

Workup

additionwas added to the solution
temperatureAfter the reaction mixture was cooled
customthe organic layer was separated
washThe organic layer was washed with water
dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
distillationdistilled under reduced pressure
customto remove the solvent
customThe residue was purified by a column chromatography (eluent; chloroform:methanol=7:1)

Sources & evidence

ORD record: ord-3532f5372dd1411a8e850f2894a88670
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129535B2

Linked notes

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