Water → Tert-butyl 4-[4-(3-chlorophenyl)-1,3-thiazol-2-yl]piperazine-1-carboxylate

HRID 2263273Notes

Reaction equation

HRID 2263273 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[CH:8]=2)[N:6]=1.[N:14]1([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:13][C:9]1[CH:8]=[C:7]([C:5]2[N:6]=[C:2]([N:17]3[CH2:16][CH2:15][N:14]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19][CH2:18]3)[S:3][CH:4]=2)[CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 457899822-Bromo-4-(3-chlorophenyl)thiazole

Product 1

HCID 68782766Tert-butyl 4-[4-(3-chlorophenyl)-1,3-thiazol-2-yl]piperazine-1-carboxylateYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-bromo-4-(3-chlorophenyl)-1,3-thiazole (6.36 g, 23.2 mmol), tert-butyl piperazine-1-carboxylate (6.47 g, 34.7 mmol) and potassium carbonate (3.20 g, 23.2 mmol) in dimethylformamide (80 ml) was stirred at 120° C. for 14 hours. Water was poured to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to give 5.19 g (59.0%) of the desired product as an oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-6ff34d66e2eb420399d2c9c67414cd6f
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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