Thiourea → 1-(4-(2-Aminothiazol-4-yl)piperidin-1-yl)ethanone

HRID 1972149Notes

Reaction equation

HRID 1972149 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10](=O)[CH2:11]Br)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[NH2:14][C:15]([NH2:17])=[S:16]>C(O)C>[NH2:17][C:15]1[S:16][CH:11]=[C:10]([CH:7]2[CH2:8][CH2:9][N:4]([C:1](=[O:3])[CH3:2])[CH2:5][CH2:6]2)[N:14]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 772303261-(1-Acetylpiperidin-4-yl)-2-bromoethan-1-one

Product 1

HCID 596100361-(4-(2-Aminothiazol-4-yl)piperidin-1-yl)ethanoneYield 74.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(1-acetylpiperidin-4-yl)-2-bromoethanone (2.37 g, 9.561 mmol) and thiourea (0.728 g, 9.561 mmol) were dissolved in ethanol (40 mL) and agitated at ambient temperature for 30 minutes. The mixture was heated to 80° C. and agitated an additional 1 hour. Upon cooling solvent was evaporated and the residue was distributed between 20 mL of 2M NaOH and 20 mL of chloroform. The organic phase was separated and discarded. The remaining aqueous phase (white slurry) was extracted with chloroform until all solids were extracted (4×200 mL). The organic extracts were combined, dried over magnesium sulfate and evaporated to give the desired product (1.600 g, 74.27% yield) as white solid.

Workup

  1. temperatureThe mixture was heated to 80° C.
  2. stirringagitated an additional 1 hour
  3. temperatureUpon cooling solvent
  4. customwas evaporated
  5. customThe organic phase was separated
  6. extractionThe remaining aqueous phase (white slurry) was extracted with chloroform until all solids
  7. extractionwere extracted (4×200 mL)
  8. dry with materialdried over magnesium sulfate
  9. customevaporated

Sources & evidence

ORD record
ord-94f0b3db26cd45f5b0ceaf72c754f0b2
Source dataset
uspto-grants-2013_04
Patent number
US08431713B2

Reaction notes

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