3-Chloro-2-butanone → 4,5-Dimethyl-2-(piperidin-1-yl)thiazole

HRID 2221555Notes

Reaction equation

HRID 2221555 reaction equation
[N:1]1([C:7](=[S:9])[NH2:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH:11]([CH3:15])[C:12](=O)[CH3:13].C(=O)([O-])O.[Na+]>CC(O)C>[CH3:15][C:11]1[N:8]=[C:7]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[S:9][C:12]=1[CH3:13]

Participants

5

Reactant 3

HCID 200263-Chloro-2-butanoneHCID 516892Sodium BicarbonateHCID 1551232Piperidine-1-carbothioamide

Product 1

HCID 230765394,5-Dimethyl-2-(piperidin-1-yl)thiazoleYield 99.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of piperidine-1-carbothioamide (3.00 g), 3-chloro-2-butanone (4.43 g) and 2-propanol (30 mL) was heated under reflux for 15 hrs. After concentration of the reaction mixture, saturated aqueous sodium hydrogen carbonate was added to the residue and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give 1-(4,5-dimethyl-1,3-thiazol-2-yl)piperidine as a colorless oil (4.05 g, yield 99%) from a fraction eluted with ethyl acetate-hexane (1:6, v/v).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 15 hrs
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-69efd1d0cc504740b74b1d8d741c7071
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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