Tetrahydrofuran → Benzyl 4-(4-(2-fluorophenyl)thiazol-2-yl)piperazine-1-carboxylate

HRID 2191544Notes

Reaction equation

HRID 2191544 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:6][CH2:5]1)(=[S:3])[NH2:2].Br[CH2:21][C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[F:30])=O.C(N(C(C)C)CC)(C)C.C1COCC1>O>[F:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[C:22]1[N:2]=[C:1]([N:4]2[CH2:5][CH2:6][N:7]([C:10]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:11])[CH2:8][CH2:9]2)[S:3][CH:21]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 27374492-Bromo-2'-fluoroacetophenoneHCID 57354701Benzyl 4-carbamothioylpiperazine-1-carboxylate

Product 1

HCID 15984569Benzyl 4-(4-(2-fluorophenyl)thiazol-2-yl)piperazine-1-carboxylateYield 27.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A solution of benzyl 4-thiocarbamoylpiperazine-1-carboxylate (2.7 g, 9.7 mmol), 2-bromo-1-(2-fluorophenyl)ethanone (2.1 g, 9.7 mmol), diisopropyl ethylamine (1.9 mL, 11 mmol), and THF (32 mL) was sealed in a microwave vessel and heated by microwave irradiation at 120° C. for 20 seconds. The reaction was cooled to room temperature, diluted with water, and extracted with CH2Cl2. The combined extracts were washed with water, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2, 0%-30% EtOAc/hexanes) to give benzyl 4-(4-(2-fluorophenyl)thiazol-2-yl)piperazine-1-carboxylate (1.05 g, 27% yield). LC/MS: m/z 398.3 (M+H)+ at 3.84 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. extractionextracted with CH2Cl2
  3. washThe combined extracts were washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (SiO2, 0%-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-7f3c1016cefe4ff3aec17015aee13f0f
Source dataset
uspto-grants-2012_12
Patent number
US08329702B2

Reaction notes

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