HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 1694923
Notes
Print preview

Reaction equation

HRID 1694923 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[CH3:23])([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[CH3:23])[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 66645910{2-[(2-Bromoacetyl)-(2-methylphenyl)amino]-1,1-dimethylethyl}carbamic acid t-butyl ester

Product 1

HCID 666457752,2-Dimethyl-4-(2-methylphenyl)-5-oxopiperazine-1-carboxylic acid t-butyl esterYield 71%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.3 g of potassium t-butoxide (12.0 mmol) in tetrahydrofuran (80 ml) was added to a solution of 3.2 g of {2-[(2-bromoacetyl)-(2-methylphenyl)amino]-1,1-dimethylethyl}carbamic acid t-butyl ester obtained in Example (51b) (8.0 mmol) in tetrahydrofuran (80 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=3/1) to obtain 1.8 g of the title compound (yield: 71%).

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=3/1)

Sources & evidence

ORD record
ord-a441d93579784d989bbb031a87f580d6
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08158790B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes