Sodium Chloride → Tert-butyl 4-methyl-3-oxopiperazine-1-carboxylate
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][C:10](=[O:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O=[C:16]1CNCCN1.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.[H-].[Na+].CI.[Cl-].[Na+]>CN(C)C=O>[CH3:16][N:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][C:10]1=[O:14]Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 1
Procedure
8 g of 4-t-butoxycarbonyl-2-oxopiperazine (previously prepared from 2-oxopiperazine and di-t-butyl dicarbonate) were dissolved in 80 ml of dimethylformamide. 1.92 g of sodium hydride (55%, in paraffin) were added to this solution, and the mixture was stirred at room temperature for one hour. A solution of 6.8 g of methyl iodide in 20 ml of dimethylformamide was then added, and the resulting mixture was stirred at room temperature for 3 hours. The reaction mixture was then poured into a saturated aqueous solution of sodium chloride and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by column chromatography through silica gel, eluted with ethyl acetate, to give 3.0 g of 1-methyl-2-oxo-4-t-butoxycarbonylpiperazine in the form of colorless oil.
Workup
- stirringthe resulting mixture was stirred at room temperature for 3 hours
- extractionextracted with ethyl acetate
- washThe extract was washed with water
- dry with materialdried over anhydrous magnesium sulfate
- distillationThe solvent was distilled off
- customthe residue was purified by column chromatography through silica gel
- washeluted with ethyl acetate
Sources & evidence
- ORD record
- ord-f25312bea45241829181cc6fa674b465
- Source dataset
- uspto-grants-1988_09
- Patent number
- US04771046
Reaction notes
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