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

HRID 1362680Notes

Reaction equation

HRID 1362680 reaction equation
CN(C=O)C.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:19]=[CH:20][C:21]=1[N:22]1[CH:26]=[C:25]([CH3:27])[N:24]=[CH:23]1)/[CH:11]=[C:12]1/[C:13](=[O:18])[NH:14][CH2:15][CH2:16][CH2:17]/1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[C:38]([C:42]1[CH:47]=[CH:46][C:45]([CH2:48]Cl)=[CH:44][CH:43]=1)([CH3:41])([CH3:40])[CH3:39]>C(OCC)(=O)C.O>[C:38]([C:42]1[CH:43]=[CH:44][C:45]([CH2:48][N:14]2[CH2:15][CH2:16][CH2:17]/[C:12](=[CH:11]\[C:10]3[CH:19]=[CH:20][C:21]([N:22]4[CH:26]=[C:25]([CH3:27])[N:24]=[CH:23]4)=[C:8]([O:7][CH3:6])[CH:9]=3)/[C:13]2=[O:18])=[CH:46][CH:47]=1)([CH3:41])([CH3:39])[CH3:40]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 88198Benzene, 1-(chloromethyl)-4-(1,1-dimethylethyl)-HCID 2733832Lithium HexamethyldisilazideHCID 58548909(E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]piperidin-2-one

Product 1

HCID 11690815(E)-1-(4-tert-butylbenzyl)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]piperidin-2-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a DMF (2 mL) solution of (E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]piperidin-2-one (70 mg) obtained in Example 416, lithium bis(trimethylsilyl)amide (1M THF solution, 0.47 mL) was added dropwise under ice-cooling, and the reaction solution was agitated for 30 minutes under ice-cooling. Subsequently, 1-tert-butyl-4-chloromethylbenzene (0.073 mL) was added to the reaction solution, and the reaction solution was agitated for 30 minutes under ice-cooling. Water and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. The obtained organic layer was dried with magnesium sulfate and was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system), and 37.8 mg of the title compound was obtained. The physical properties are as follows.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe reaction solution was agitated for 30 minutes under ice-
  4. temperaturecooling
  5. customthe organic layer was partitioned
  6. dry with materialThe obtained organic layer was dried with magnesium sulfate
  7. concentrationwas concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-d718b2294ef64ea09da24780dbed7666
Source dataset
uspto-grants-2011_02
Patent number
US07880009B2

Reaction notes

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