Water → HCID 58181287, compound

HRID 1465462Notes

Reaction equation

HRID 1465462 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2].Br[C:11]1[S:12][CH:13]=[C:14]([Br:16])[N:15]=1.C(N(CC)CC)C.O>CN(C)C=O>[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:11]2[S:12][CH:13]=[C:14]([Br:16])[N:15]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 837951-AcetylpiperazineHCID 27632972,4-Dibromo-1,3-thiazole

Product 1

HCID 58181287HCID 58181287, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 1-acetylpiperazine (316 mg, 4.78 mmol) and 2,4-dibromo-1,3-thiazole (900 mg, 3.71 mmol) in N,N-dimethylformamide (8 ml) was added triethylamine (0.78 ml, 5.56 mmol). The reaction mixture was stirred at 50° C. for 14 hrs and at 65° C. for 6 hrs. After cooling to room temperature, the reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The combined organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (dichloromethane:methanol=100:0→98:2) to give 1-acetyl-4-(4-bromo-1,3-thiazol-2-yl)piperazine (590 mg, yield 55%) as a pale-white brown solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe combined organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (dichloromethane:methanol=100:0→98:2)

Sources & evidence

ORD record
ord-14cc0f9311fc4591b9bef5b91ed06083
Source dataset
uspto-grants-2015_04
Patent number
US08999989B2

Reaction notes

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