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

HRID 2263261
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Reaction equation

HRID 2263261 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:8]=2[F:14])[N:6]=1.[N:15]1([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[F:14][C:8]1[C:9]([F:13])=[CH:10][CH:11]=[CH:12][C:7]=1[C:5]1[N:6]=[C:2]([N:18]2[CH2:17][CH2:16][N:15]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][CH2:19]2)[S:3][CH:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 687769562-Bromo-4-(2,3-difluorophenyl)-1,3-thiazole

Product 1

HCID 68781293Tert-butyl 4-[4-(2,3-difluorophenyl)-1,3-thiazol-2-yl]piperazine-1-carboxylateYield 45.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-bromo-4-(2,3-difluorophenyl)-1,3-thiazole (6.74 g, 24.4 mmol), tert-butyl piperazine-1-carboxylate (9.09 g, 48.4 mmol) and potassium carbonate (3.37 g, 24.4 mmol) in dimethylformamide (80 ml) was stirred at 120° C. for 13 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. Hexane was added to the residue, and crystals were collected by filtration to give 4.20 g (45.1%) of the desired product as a solid.

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. additionHexane was added to the residue, and crystals
  6. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-96844dbf61da4f8995c7ab030a8ab63d
Source dataset
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07851473B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes