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Ammonium Chloride → 4-(2-Chlorophenyl)-2,2-dimethyl-5-oxopiperazine-1-carboxylic acid t-butyl ester

HRID 1694891
Notes
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Reaction equation

HRID 1694891 reaction equation
CC(C)([O-])C.[K+].[C:7]([O:11][C:12](=[O:30])[NH:13][C:14]([CH3:29])([CH3:28])[CH2:15][N:16]([C:24](=[O:27])[CH2:25]Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[Cl:23])([CH3:10])([CH3:9])[CH3:8].[Cl-].[NH4+]>O1CCCC1.O>[C:7]([O:11][C:12]([N:13]1[CH2:25][C:24](=[O:27])[N:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])[CH2:15][C:14]1([CH3:29])[CH3:28])=[O:30])([CH3:10])([CH3:9])[CH3:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 66645498{2-[(2-Bromoacetyl)-(2-chlorophenyl)amino]-1,1-dimethylethyl}carbamic acid t-butyl ester

Product 1

HCID 666454674-(2-Chlorophenyl)-2,2-dimethyl-5-oxopiperazine-1-carboxylic acid t-butyl esterYield 81%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.87 g of potassium t-butoxide (16.7 mmol) in tetrahydrofuran (110 ml) was added to a solution of 4.68 g of {2-[(2-bromoacetyl)-(2-chlorophenyl)amino]-1,1-dimethylethyl}carbamic acid t-butyl ester obtained in Example (1i) (11.2 mmol) in tetrahydrofuran (110 ml) under a nitrogen atmosphere and under cooling in a dry ice-acetone bath over 30 minutes, and the mixture was stirred at the same temperature for 10 minutes. A saturated ammonium chloride aqueous solution was added to the reaction mixture. The mixture was returned to room temperature and diluted with water, followed by extraction with ethyl acetate. Then, the organic layer was dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent:hexane/ethyl acetate=2/1) to obtain 3.07 g of the title compound (yield: 81%).

Workup

  1. temperatureunder cooling in a dry ice-acetone bath over 30 minutes
  2. customwas returned to room temperature
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThen, the organic layer was dried over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (elution solvent:hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-63fe92cf022f4d14a8617d3193ab3f12
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08158790B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes