Triethylamine → 1-Diethylamino ethyl-2-phenyl-3-keto piperazine

HRID 596853Notes

Reaction equation

HRID 596853 reaction equation
[C:1]1([CH:7]2[C:12](=[O:13])[NH:11][CH2:10][CH2:9][NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:14]([N:16]([CH2:19][CH2:20]Cl)[CH2:17][CH3:18])[CH3:15].C(N(CC)CC)C>CC(C)=O>[CH2:14]([N:16]([CH2:19][CH3:20])[CH:17]([N:8]1[CH2:9][CH2:10][NH:11][C:12](=[O:13])[CH:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH3:18])[CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13364Diethylaminoethyl chlorideHCID 2506813-Phenylpiperazin-2-one

Product 1

HCID 214485351-Diethylamino ethyl-2-phenyl-3-keto piperazineYield 64%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

144 g. of 2-phenyl-3-keto piperazine are boiled under reflux with 121 g. of diethylamino ethylchloride, 340 cc. of triethylamine, and 1600 cc. of acetone for 24 hours. The cooled solution is filtered to remove triethylamine hydrochloride and the filtrate is evaporated to dryness. The residue is dissolved in water, 40 % sodium hydroxide solution is added thereto, and the oil which forms as upper layer, is extracted with benzene. The benzene solution is dried over anhydrous potassium carbonate, the benzene is removed by distillation, and the residue is distilled in a vacuum. A light yellow, viscous oil of the boiling point 175° C./0.05 mm. Hg is obtained. The oil is twice recrystallized from n-heptane. 145 g. of the above mentioned compound melting at 53°-56° C. are obtained. The yield is 64 % of the theoretical yield.

Workup

  1. temperatureunder reflux with 121 g
  2. filtrationThe cooled solution is filtered
  3. customto remove triethylamine hydrochloride
  4. customthe filtrate is evaporated to dryness
  5. dissolutionThe residue is dissolved in water
  6. addition40 % sodium hydroxide solution is added
  7. extractionis extracted with benzene
  8. dry with materialThe benzene solution is dried over anhydrous potassium carbonate
  9. customthe benzene is removed by distillation
  10. distillationthe residue is distilled in a vacuum
  11. customA light yellow, viscous oil of the boiling point 175° C./0.05 mm. Hg is obtained
  12. customThe oil is twice recrystallized from n-heptane
  13. customare obtained

Sources & evidence

ORD record
ord-41e0dcda606e4611ad34a038ae6032bf
Source dataset
uspto-grants-1977_03
Patent number
US04012389

Reaction notes

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