Dimethylformamide → [4-(5-Bromothiazole-2-yl)-2,6-dimethyl piperazine-1-yl]acetic acid methyl ester
Reaction equation
[Br:1][C:2]1[S:6][C:5]([N:7]2[CH2:12][CH:11]([CH3:13])[NH:10][CH:9]([CH3:14])[CH2:8]2)=[N:4][CH:3]=1.[CH3:15][O:16][C:17](=[O:20])[CH2:18]Br.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:15][O:16][C:17](=[O:20])[CH2:18][N:10]1[CH:11]([CH3:13])[CH2:12][N:7]([C:5]2[S:6][C:2]([Br:1])=[CH:3][N:4]=2)[CH2:8][CH:9]1[CH3:14]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A mixture of 1-(5-bromothiazole-2-yl)-3,5-dimethyl piperazine (21.5 g), bromo acetic acid methyl ester (8.8 mL), potassium carbonate (12.9 g) and dimethylformamide (150 mL) was stirred at 60° C. for 2.5 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 magnesium sulphate. The solvent was evaporated under reduced pressure. The residue was purified by column chromatograph on silica gel to give the title compound (20.1 g). Yield: 74%.
Workup
- extractionextracted with ethyl acetate
- washThe organic layer was washed with water and brine
- dry with materialdried over magnesium sulphate
- customThe solvent was evaporated under reduced pressure
- customThe residue was purified by column chromatograph on silica gel
Sources & evidence
- ORD record
- ord-4b0c471c13cf41f4a78151cb8d894c33
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08097610B2
Reaction notes
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