3-Chloro-2-methyl-1-propene → HCID 22038362, compound

HRID 1790530Notes

Reaction equation

HRID 1790530 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].Cl[CH2:20][C:21]([CH3:23])=[CH2:22].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([N:10]([CH2:22][C:21]([CH3:23])=[CH2:20])[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 112413-Chloro-2-methyl-1-propeneHCID 11430Potassium CarbonateHCID 22037924HCID 22037924, compound

Product 1

HCID 22038362HCID 22038362, compoundYield 63.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of N-(l-acetylpiperidin-4-yl)-3-methoxyaniline (2.0 g), 3-chloro-2-methylpropene (10 ml) and potassium carbonate (5.0 g) in dimethylformamide (50 ml) was reacted at 80° C. for 6 hr. Then the reaction mixtures were concentrated under reduced pressure and partitioned between ethyl acetate and water. The ethyl acetate layer was washed successively with water and brine and dried over magnesium sulfate. After evaporating the solvent under reduced pressure, the residue was purified by silica gel column chromatography (ethyl acetate/hexane system) to give the title compound (1.55 g) as a yellow oil (yield: 63.6%).

Workup

  1. customwas reacted at 80° C. for 6 hr
  2. customThen the reaction mixtures
  3. concentrationwere concentrated under reduced pressure
  4. custompartitioned between ethyl acetate and water
  5. washThe ethyl acetate layer was washed successively with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customAfter evaporating the solvent under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane system)

Sources & evidence

ORD record
ord-8523842c5ee249419d04ca9122dbe120
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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