Ethylenediamine → 3-(Propan-2-yl)piperazin-2-one

HRID 1968610Notes

Reaction equation

HRID 1968610 reaction equation
Br[CH:2]([CH:8]([CH3:10])[CH3:9])[C:3]([O:5]CC)=O.[CH2:11]([NH2:14])[CH2:12][NH2:13].[O-]CC.[Na+]>C(O)C>[CH:8]([CH:2]1[NH:14][CH2:11][CH2:12][NH:13][C:3]1=[O:5])([CH3:9])[CH3:10]

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 79068Ethyl 2-bromoisovalerateHCID 2723922Sodium ethoxide

Product 1

HCID 448908153-(Propan-2-yl)piperazin-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

Ethyl 2-bromo-3-methylbutanoate (2.2 g, 10.52 mmol) in ethanol (15 mL) was added dropwise over a period of 2.5 hours to a stirred refluxing solution of ethane-1,2-diamine (13.2 mL, 197 mmol) in ethanol (60 mL). The mixture was heated for another 2.5 hours, and sodium ethoxide in ethanol (21% by wt) (4.0 mL, 10.80 mmol) was added and the mixture was heated for another 90 minutes. The reaction was then cooled and concentrated. After trituration with ether, the title compound was used in the next step without further purification.

Workup

  1. temperatureThe mixture was heated for another 2.5 hours
  2. temperaturethe mixture was heated for another 90 minutes
  3. temperatureThe reaction was then cooled
  4. concentrationconcentrated
  5. customAfter trituration with ether, the title compound was used in the next step without further purification

Sources & evidence

ORD record
ord-b1a8e518efab4f4d9a7b2693ab592d85
Source dataset
uspto-grants-2013_04
Patent number
US08426422B2

Reaction notes

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