Ethylenediamine → 2-Piperazinone, 3,3-dimethyl-

HRID 43140

Reaction equation

HRID 43140 reaction equation
C(O[C:4](=[O:9])[C:5](Br)([CH3:7])[CH3:6])C.[CH2:10]([NH2:13])[CH2:11][NH2:12].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[CH3:7][C:5]1([CH3:6])[NH:13][CH2:10][CH2:11][NH:12][C:4]1=[O:9]

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl ester

Product 1

HCID 2111572-Piperazinone, 3,3-dimethyl-Yield 68.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
115 °C

Procedure

A solution of ethyl-2-bromoisobutyrate (24 mL, 161 mmol) in toluene (150 mL) was added to a mixture of ethylene diamine (70 mL, 1046 mmol, 6.5 equiv) and potassium carbonate (24.4 g, 177 mmol, 1.1 equiv) in toluene (150 mL). The reaction mixture was heated for 20 h at 115° C., cooled and filtered. The filtrate was concentrated and the residue triturated in Et2O to afford 14.2 g of the title compound as a yellow solid: ESI-MS: 129.1 [M+H]+.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. customthe residue triturated in Et2O

Sources & evidence

ORD record
ord-b6f1359851554a6e8633af1cffc9717a
Source dataset
uspto-grants-2013_09
Patent number
US08536175B2

Linked notes

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