Acetone → HCID 67976957, compound

HRID 2174476Notes

Reaction equation

HRID 2174476 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:5][C:3]=1[NH2:4].CC(C)=O.C([O-])([O-])=O.[K+].[K+].[C:28](Cl)(=[O:37])[CH:29]=[CH:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>O>[Cl:1][C:2]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:5][C:3]=1[NH:4][C:28](=[O:37])[CH:29]=[CH:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 660233-Phenylprop-2-enoyl chlorideHCID 67975039HCID 67975039, compound

Product 1

HCID 67976957HCID 67976957, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-chloro-5-(2-piperidinoethoxy)aniline (500 mg, 1.9 mmol, 1 eq.) was placed in mixture of acetone (653 μL) and water (852 μL) in the presence of K2CO3(541 m g, 3.9 mmol, 2 eq.). Cinnamoyl chloride (326 mg, 1.9 mmol, 1 eq.) was then added at 0° C. The reaction mixture was allowed to warm-up to room temperature, stirred for 2 hours and extracted with ethyl acetate. The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel to afford N-(2-chloro-5-(2-(piperidin-1-yl)ethoxy)phenyl)cinnamamide (521 mg, 69%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-e148d0c7125a4ad3aedca1efe7cffb91
Source dataset
uspto-grants-2015_06
Patent number
US09061999B2

Reaction notes

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