Water → 1-(3-(2-(1-Benzothiophene-5-yl)ethoxy)propyl)-3-pyrrolidinol

HRID 2377157

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[CH2:21][CH2:20][CH:19]([OH:22])[CH2:18]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.C(OCC)(=O)C>[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[CH2:21][CH2:20][CH:19]([OH:22])[CH2:18]3)=[CH:16][C:12]=2[CH:13]=[CH:14]1

Participants

Conditions

Temperature: 85 °C

Procedure

In 12 mL of N,N-dimethylformamide was dissolved 1.20 g of 5-[2-(3-chloropropoxy)ethyl]-1-benzothiophene, and 0.82 g of 3-pyrrolidinol and 1.30 g of potassium carbonate were added to the solution, after which the resulting mixture was stirred at 85° C. for 2.5 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 20:1 to 10:1) to obtain 0.78 g of 1-{3-[2-(1-benzothiophen-5-yl)ethoxy]propyl}-3-pyrrolidinol as a colorless oil.

Workup

additionwere 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 20:1 to 10:1)

Sources & evidence

ORD record: ord-00ab880a920c4cc98bafb2f73b92c8a6
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07468443B2

Linked notes

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