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Triethylamine → 1-(2-Methoxymethoxyphenyl)-5,5-dimethylpiperazin-2-one

HRID 1694909
Notes
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Reaction equation

HRID 1694909 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 85247Trimethylsilyl iodideHCID 516892Sodium BicarbonateHCID 666457882,2-Dimethyl-4-(2-methoxymethoxyphenyl)-5-oxopiperazine-1-carboxylic acid t-butyl ester

Product 1

HCID 666456561-(2-Methoxymethoxyphenyl)-5,5-dimethylpiperazin-2-oneYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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

  1. extractionfollowed by extraction with methylene chloride
  2. washThen, the organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated under reduced pressure
  6. 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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08158790B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes