1,3-Dichloroacetone → HCID 57423801, compound

HRID 2063436Notes

Reaction equation

HRID 2063436 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14](=[S:16])[NH2:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:17][CH2:18][C:19]([CH2:21]Cl)=O.[O-]S([O-])(=O)=O.[Mg+2]>CC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]2[S:16][CH:21]=[C:19]([CH2:18][Cl:17])[N:15]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 107931,3-DichloroacetoneHCID 24083Sulfuric acid magnesium salt (1:1)HCID 23546083tert-Butyl 3-carbamothioylpiperidine-1-carboxylate

Product 1

HCID 57423801HCID 57423801, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3-Thiocarbamoyl-piperidine-1-carboxylic acid tert-butyl ester (2.2 g, 9.02 mmol) in acetone (45 mL) was added 1,3-dichloroacetone (1.49 g, 11 7 mmol), MgSO4 (1.63 g, 13.5 mmol) and MgCO3 (0.76 g, 9.02 mmol). The mixture was heated under reflux overnight, cooled and filtered through celite. The solvent was removed in vacuo and the residue was redissolved with EtOAc (20 mL). The resulting solution was washed successively with 5% NaHSO3, saturated NaHCO3, and brine. After drying (Na2SO4), the solvent was removed to afford the desired product which was used without further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux overnight
  3. temperaturecooled
  4. filtrationfiltered through celite
  5. customThe solvent was removed in vacuo
  6. dissolutionthe residue was redissolved with EtOAc (20 mL)
  7. washThe resulting solution was washed successively with 5% NaHSO3, saturated NaHCO3, and brine
  8. dry with materialAfter drying (Na2SO4)
  9. customthe solvent was removed

Sources & evidence

ORD record
ord-5c0164f2310c4b799a7663c24754e68a
Source dataset
uspto-grants-2012_10
Patent number
US08288384B2

Reaction notes

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