3-Chloro-2-butanone → Ethyl 1-(4,5-dimethyl-1,3-thiazol-2-yl)piperidine-4-carboxylate

HRID 2221637Notes

Reaction equation

HRID 2221637 reaction equation
[NH2:1][C:2]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:6][CH2:5]1)=[S:3].Cl[CH:16]([CH3:20])[C:17](=O)[CH3:18]>CC(O)C>[CH3:20][C:16]1[N:1]=[C:2]([N:4]2[CH2:9][CH2:8][CH:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:6][CH2:5]2)[S:3][C:17]=1[CH3:18]

Participants

4

Reactant 2

HCID 200263-Chloro-2-butanoneHCID 23076419Ethyl 1-carbamothioylpiperidine-4-carboxylate

Product 1

HCID 23076351Ethyl 1-(4,5-dimethyl-1,3-thiazol-2-yl)piperidine-4-carboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of ethyl 1-(aminocarbonothioyl)piperidine-4-carboxylate (5.85 g), 3-chloro-2-butanone (5.75 g) and 2-propanol (100 mL) was heated under reflux for 15 hrs, and concentrated. Ethyl acetate was added to the residue. The ethyl acetate layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried ver anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:4, v/v) to give ethyl 1-(4,5-dimethyl-1,3-thiazol-2-yl)piperidine-4-carboxylate as a colorless oil (6.86 g, yield 95%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 15 hrs
  3. concentrationconcentrated
  4. additionEthyl acetate was added to the residue
  5. washThe ethyl acetate layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine
  6. dry with materialdried ver anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. washeluted with ethyl acetate-hexane (1:4, v/v)

Sources & evidence

ORD record
ord-d32573b791b04919857a40eb9385a18e
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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