Hydrochloric Acid → 1,4-Bis(phenylmethyl)piperazinone, hydrochloride

HRID 1981609Notes

Reaction equation

HRID 1981609 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][NH:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:19]CC([O:23][CH2:24][CH3:25])=O.C(=O)([O-])[O-].[Na+].[Na+].Cl>C(O)C.C(O)(C)C>[ClH:19].[C:13]1([CH2:12][N:11]2[CH2:10][CH2:9][N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:25][C:24]2=[O:23])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7751Ethyl chloroacetateHCID 8793BenzathineHCID 10340Sodium Carbonate

Product 1

HCID 233196591,4-Bis(phenylmethyl)piperazinone, hydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3776IsopropanolSolvent

Procedure

A mixture of N,N'-dibenzylethylenediamine (24.0 g., 0.1 mole), ethyl chloroacetate (V, 24.51 g., 0.2 mole), anhydrous sodium carbonate (10 g., 0.094 mole) in ethanol (250 ml.) is heated under reflux for 20 hours. The ethanol is removed under reduced pressure and the residue is partitioned between chloroform and water. Evaporation of the chloroform gives an oil which is dissolved in isopropanol (200 ml.) and acidified with ethereal hydrogen chloride. The precipitate of 1,4-bis(phenylmethyl)piperazinone hydrochloride is filtered off and recrystallized from isopropanol, m.p. 209°-212°.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 20 hours
  3. customThe ethanol is removed under reduced pressure
  4. customthe residue is partitioned between chloroform and water
  5. customEvaporation of the chloroform
  6. customgives an oil which
  7. filtrationThe precipitate of 1,4-bis(phenylmethyl)piperazinone hydrochloride is filtered off
  8. customrecrystallized from isopropanol, m.p. 209°-212°

Sources & evidence

ORD record
ord-72e9da7095cb4ed9a8a2c7255e80743f
Source dataset
uspto-grants-1986_06
Patent number
US04593098

Reaction notes

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