Ethylenediamine → HCID 13520416, compound

HRID 484977Notes

Reaction equation

HRID 484977 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].Br[CH:6]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]([O:9]CC)=O>C1COCC1.C(O)C>[C:13]1([CH2:12][CH:6]2[NH:4][CH2:1][CH2:2][NH:3][C:7]2=[O:9])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 3301EthylenediamineHCID 4737529Ethyl 2-bromo-3-phenylpropanoate

Product 1

HCID 13520416HCID 13520416, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethylenediamine (25 g.) is added to a stirred solution of ethyl 2-bromo-3-phenylpropionate (XXVII, Example 61, 14.0 g.) in THF (100 ml.) and ethanol (300 ml.). After 20 hours at 20°-25° the solvents are removed under reduced pressure and the residual oil is partitioned between ethyl acetate-1N sodium hydroxide solution. The ethyl acetate extract is washed with water, saline, and concentrated. The residual oil is applied to a silica gel column which is eluted with chloroform-methanol (9/1). Fractions containing the product are pooled, concentrated to a residue and recrystallized from ethyl acetate-SSB to give 3-(phenylmethyl)piperazinone, m.p. 92°-93°.

Workup

  1. customAfter 20 hours at 20°-25° the solvents are removed under reduced pressure
  2. customthe residual oil is partitioned between ethyl acetate-1N sodium hydroxide solution
  3. extractionThe ethyl acetate extract
  4. washis washed with water, saline
  5. concentrationconcentrated
  6. washis eluted with chloroform-methanol (9/1)
  7. additionFractions containing the product
  8. concentrationconcentrated to a residue
  9. customrecrystallized from ethyl acetate-SSB

Sources & evidence

ORD record
ord-8a031eacf8c7404aa5696f39937a5915
Source dataset
uspto-grants-1985_08
Patent number
US04534897

Reaction notes

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