Water → (E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]piperidin-2-one

HRID 2247520Notes

Reaction equation

[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[N:13]1[CH:17]=[C:16]([CH3:18])[N:15]=[CH:14]1)[CH:8]=O.C([N:22]1[CH2:27][CH2:26][CH2:25][CH2:24][C:23]1=[O:28])(=O)C.O>C1COCC1.CN(C=O)C>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[N:13]1[CH:17]=[C:16]([CH3:18])[N:15]=[CH:14]1)/[CH:8]=[C:24]1/[C:23](=[O:28])[NH:22][CH2:27][CH2:26][CH2:25]/1

Participants

Conditions

Temperature: 0 °C

Procedure

To a sodium hydride suspension (40% mineral oil content, 2.77 g) in THF (50 mL) and DMF (200 mL), a solution of 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (10 g) obtained in Example 1 and 1-acetylpiperidin-2-one (7.17 g) in THF (50 mL) and DMF (200 mL) were added dropwise over 20 minutes at 5° C. This reaction solution was agitated at 0° C. for 2 hours. The reaction solution was added to iced water and the reaction solution was extracted with ethyl acetate. The obtained organic layer was washed with a saturated sodium chloride solution, and concentrated under reduced pressure after dried over anhydrous magnesium sulfate. The deposited solids were separated by filtering and 5.0 g of the title compound was obtained by washing with diethyl ether. The physical properties of the compound are as follows.

Workup

extractionthe reaction solution was extracted with ethyl acetate
washThe obtained organic layer was washed with a saturated sodium chloride solution
concentrationconcentrated under reduced pressure
dry with materialafter dried over anhydrous magnesium sulfate
customThe deposited solids were separated
filtrationby filtering

Sources & evidence

ORD record: ord-ee8f3eefb2f4457084f0d31b9c177fc9
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687640B2

Reaction notes

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