1,3-Dichloroacetone → 1-(4-(Chloromethyl)-1,3-thiazol-2-yl)piperidine

HRID 2221550Notes

Reaction equation

HRID 2221550 reaction equation
[N:1]1([C:7](=[S:9])[NH2:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:10][CH2:11][C:12](=O)[CH2:13]Cl.C(=O)([O-])O.[Na+]>C(O)C>[Cl:10][CH2:11][C:12]1[N:8]=[C:7]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[S:9][CH:13]=1

Participants

5

Reactant 3

HCID 107931,3-DichloroacetoneHCID 516892Sodium BicarbonateHCID 1551232Piperidine-1-carbothioamide

Product 1

HCID 225634051-(4-(Chloromethyl)-1,3-thiazol-2-yl)piperidineYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of piperidine-1-carbothioamide (1.0 g), 1,3-dichloro-2-propanone (0.91 g) and ethanol (30 mL) was heated under reflux for 1 hr. 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 ethyl acetate 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-chloromethyl-1,3-thiazol-2-yl)piperidine as a colorless oil (1.00 g, yield 67%) from a fraction eluted with ethyl acetate-hexane (1:4, v/v).

Workup

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

Sources & evidence

ORD record
ord-c203cafcf3fd4af5b384cd57619ad526
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

Loading…