Triethylamine → 1-(2-Methoxymethoxyphenyl)-5,5-dimethylpiperazin-2-one
Reaction equation
C(N(CC)CC)C.I[Si](C)(C)C.C(OC([N:20]1[CH2:25][C:24](=[O:26])[N:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33][CH2:34][O:35][CH3:36])[CH2:22][C:21]1([CH3:38])[CH3:37])=O)(C)(C)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:36][O:35][CH2:34][O:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[N:23]1[CH2:22][C:21]([CH3:37])([CH3:38])[NH:20][CH2:25][C:24]1=[O:26]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
0.58 ml of triethylamine (4.10 mmol) and 0.3 ml of iodotrimethylsilane (2.05 mmol) were added to a solution of 497 mg of 4-(2-methoxymethoxyphenyl)-2,2-dimethyl-5-oxopiperazine-1-carboxylic acid t-butyl ester obtained in the above reaction (1.36 mmol) in methylene chloride (14 ml), and the mixture was stirred at 0° C. for 30 minutes. A saturated sodium bicarbonate aqueous solution was added to the reaction mixture, followed by extraction with methylene chloride. Then, the organic layer was washed with brine and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by basic silica gel (NH type) column chromatography (elution solvent: methylene chloride/methanol=20/1) to obtain 310 mg of the title compound (yield: 86%).
Workup
- extractionfollowed by extraction with methylene chloride
- washThen, the organic layer was washed with brine
- dry with materialdried over anhydrous sodium sulfate
- filtrationAfter filtration
- customthe solvent was evaporated under reduced pressure
- customthe residue was purified by basic silica gel (NH type) column chromatography (elution solvent: methylene chloride/methanol=20/1)
Sources & evidence
- ORD record
- ord-1b03f9290ad44042a6756f342d4d537d
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08158790B2
Reaction notes
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