Water → HCID 21990094, compound

HRID 7449Notes

Reaction equation

[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][O:12][CH2:13][CH2:14][CH2:15][N:16]3[CH2:20][CH2:19][CH:18]([NH2:21])[CH2:17]3)=[CH:9][C:4]=2[CH:3]=[CH:2]1.C(N(CC)CC)C.[C:29](Cl)(=[O:31])[CH3:30].O>C(Cl)Cl.C(OCC)(=O)C>[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][O:12][CH2:13][CH2:14][CH2:15][N:16]3[CH2:20][CH2:19][CH:18]([NH:21][C:29](=[O:31])[CH3:30])[CH2:17]3)=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

Conditions

Temperature: -60 °C

Procedure

In 5 mL of methylene chloride was dissolved 0.50 g of 1-{3-[2-(1-benzothiophen-5-yl)ethoxy]propyl}-3-pyrrolidinamine, and the solution was cooled to −60° C., after which 0.27 mL of triethylamine and 0.14 mL of acetyl chloride were added to the solution and the resulting mixture was stirred at room temperature for 1 hour. Water and ethyl acetate were added to the reaction mixture and the organic layer was separated. The organic layer was washed with 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=50:1 to 10:1) to obtain 0.55 g of N-(1-{3-[2-(1-benzothiophen-5-yl)ethoxy]propyl}-3-pyrrolidinyl)acetamide as a yellow oil.

Workup

customthe organic layer was separated
washThe organic layer was washed with a saturated aqueous sodium chloride solution
dry with materialdried over anhydrous magnesium sulfate
distillationdistilled under reduced pressure
customto remove the solvent
customThe residue was purified by a column chromatography (eluent; chloroform:methanol=50:1 to 10:1)

Sources & evidence

ORD record: ord-d4d75afba23847729c07533600501544
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07087594B2

Reaction notes

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