Isopropylamine → 2-(3-benzyloxybenzoyl)-N-isopropyl-3-phenylacryl amide

HRID 17884

Reaction equation

C(O[C:4](=[O:22])[CH2:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:9]=1)=[O:7])C.[CH:23]([NH2:26])([CH3:25])[CH3:24]>C1(C)C=CC=C(C)C=1>[CH2:15]([O:14][C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][CH:11]=1)[C:6]([C:5](=[CH:6][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:4]([NH:26][CH:23]([CH3:25])[CH3:24])=[O:22])=[O:7])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 150 °C

Procedure

3-(3-Benzyloxyphenyl)-3-oxopropionate ethyl ester (174.42 g, 584.47 mmol) was dissolved in m-xylene and the reaction mixture was refluxed while stirring for 30 min at 150° C. Then, isopropylamine (38 g, 642.92 mmol) was added dropwise to the mixture. After stirring and refluxing for 24 hours at room temperature, the organic layer was extracted with saturated sodium chloride and ethyl acetate, dried over anhydrous magnesium sulfate, concentrated, and resulting residue was purified by column chromatography (ethyl acetate:hexane=1:2) to obtain 2-(3-benzyloxybenzoyl)-N-isopropyl-3-phenylacryl amide (127.13 g, yield 70%) as yellow oil.

Workup

temperaturethe reaction mixture was refluxed
stirringAfter stirring
temperaturerefluxing for 24 hours at room temperature
extractionthe organic layer was extracted with saturated sodium chloride and ethyl acetate
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated
customresulting residue
customwas purified by column chromatography (ethyl acetate:hexane=1:2)

Sources & evidence

ORD record: ord-6f30f4c684614fd5b1c8d02605a5658c
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741323B2

Linked notes

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