Water → HCID 21990094, compound

HRID 597821Notes

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

0.50 g of 1-(3-(2-(1-benzothiophene-5-yl)ethoxy)propyl)-3-pyrrolidinamine was dissolved in 5 ml of methylene chloride. The obtained solution was cooled to −60° C. Thereafter, 0.27 ml of triethylamine and 0.14 ml of acetyl chloride were added thereto, and the obtained mixture was stirred at a room temperature for 1 hour. Thereafter, water and ethyl acetate were added to the reaction mixture, and an organic layer was then separated. The organic layer was washed with a saturated saline solution and then dried over anhydrous magnesium sulfate. The solvent was then distilled away under a reduced pressure. The residue was purified by column chromatography (eluent; chloroform:methanol=50:1 to 10:1), so as to obtain 0.55 g of a yellow oil product, N-(1-(3-(2-(1-benzothiophene-5-yl)ethoxy)propyl)-3-pyrrolidinyl)acetamide.

Workup

customan organic layer was then separated
washThe organic layer was washed with a saturated saline solution
dry with materialdried over anhydrous magnesium sulfate
distillationThe solvent was then distilled away under a reduced pressure
customThe residue was purified by column chromatography (eluent; chloroform:methanol=50:1 to 10:1)

Sources & evidence

ORD record: ord-cee20684df424265b31bbaca6c319465
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897594B2

Reaction notes

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