Isopropyl iodide → HCID 10423169, compound

HRID 1783313Notes

Reaction equation

HRID 1783313 reaction equation
[NH:1]1[CH2:6][CH:5]=[C:4]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[NH:9][CH:8]=2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[CH:24](I)([CH3:26])[CH3:25]>C(#N)C.O>[CH:24]([N:1]1[CH2:2][CH:3]=[C:4]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[NH:9][CH:8]=2)[CH2:5][CH2:6]1)([CH3:26])[CH3:25]

Participants

6

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 10421246HCID 10421246, compound

Product 1

HCID 10423169HCID 10423169, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

4-(1,2,3,6-Tetrahydropyridin-4-yl)-2H-isoquinolin-1-one (0.4 g) obtained in Example 205 and potassium carbonate (1 g) were suspended in acetonitrile (10 mL) and water (1 mL), and isopropyl iodide (0.35 mL) was added at room temperature. The mixture was stirred under heating overnight at 40° C. After the completion of the reaction, the solvent was evaporated. Aqueous potassium carbonate solution was added to the obtained residue, and the mixture was extracted with chloroform. The organic layer was dried over magnesium sulfate, and the solvent was evaporated. The obtained residue was subjected to silica gel column chromatography (NH silica gel, Fuji Silysia Chemical Ltd.). The fraction eluted with chloroform:methanol=25:1 was concentrated, and the precipitated crystals were collected by filtration to give 4-(1-isopropyl-1,2,3,6-tetrahydropyridin-4-yl)-2H-isoquinolin-1-one.

Workup

  1. customAfter the completion of the reaction
  2. customthe solvent was evaporated
  3. additionAqueous potassium carbonate solution was added to the obtained residue
  4. extractionthe mixture was extracted with chloroform
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. customthe solvent was evaporated
  7. washThe fraction eluted with chloroform
  8. concentrationmethanol=25:1 was concentrated
  9. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-2f29c37076ab4202b31983e93ade142b
Source dataset
uspto-grants-2009_03
Patent number
US07501412B2

Reaction notes

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