Dimethylformamide → 1-(5-Bromothiazole-2-yl)-3,5-dimethyl piperazine

HRID 420567Notes

Reaction equation

HRID 420567 reaction equation
Br[C:2]1[S:3][C:4]([Br:7])=[CH:5][N:6]=1.[CH3:8][CH:9]1[CH2:14][NH:13][CH2:12][CH:11]([CH3:15])[NH:10]1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Br:7][C:4]1[S:3][C:2]([N:13]2[CH2:12][CH:11]([CH3:15])[NH:10][CH:9]([CH3:8])[CH2:14]2)=[N:6][CH:5]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 660562,6-DimethylpiperazineHCID 3123942,5-Dibromothiazole

Product 1

HCID 666579111-(5-Bromothiazole-2-yl)-3,5-dimethyl piperazineYield 64.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2,5-dibromothiazole (29.5 g), 2,6-dimethyl piperazine (13.8 g), potassium carbonate (20.1 g) and dimethylformamide (150 mL) was stirred at 60° C. for 6 hours. To the reaction solution was added water and extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over sodium sulphate. The solvent was evaporated under reduced pressure to give the title compound (21.5 g). Yield: 64%.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over sodium sulphate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9c5ae5c80b0f45c39ac6c1c9530de267
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

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