Hydrogen Bromide → 1-(2-Phenoxy-2-methylpropionyl)piperazine hydrochloride

HRID 482484Notes

Reaction equation

HRID 482484 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br.[O:8]([C:15]([CH3:20])([CH3:19])[C:16]([Cl:18])=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CCO.O.C1COCC1>[ClH:18].[O:8]([C:15]([CH3:20])([CH3:19])[C:16]([N:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 3

HCID 260Hydrogen BromideHCID 4837PiperazineHCID 131111912-Methyl-2-phenoxypropanoyl chloride

Product 1

HCID 190630911-(2-Phenoxy-2-methylpropionyl)piperazine hydrochloride

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 17.2 g of anhydrous piperazine in 50 ml of EtOH 95% and 22 ml of H2O, 3.37 g of HBr 48% are dropped in about 10' and thereafter, in about 40' and at room temperature, a solution of 9.93 g of 2-phenoxy-2-methylpropionyl chloride (prepared according to: Bull. Soc. Chim. Fr. 1956, 776-783) in 70 ml of THF. The suspension is stirred 2 h at the same temperature and 3 h under reflux, diluted with 130 ml of THF, cooled, and the piperazine salts precipitated are filtered away. The filtered is evaporated to dryness, the residue is resuspended with 120 ml of H2O and 35 ml HCl 2N and extracted with Et2O; the aqueous phase is treated with 40 ml NaOH conc. and extracted with Et2O (4×50 ml). The ethere-phase, dried, is treated with HCl in Et2 O about 3N and the precipitate is collected by filtration and crystallized from EtOH giving 5.98 g (42%) of the wanted compound; m.p.: 236°-238° C.

Workup

  1. temperatureunder reflux
  2. temperaturecooled
  3. customthe piperazine salts precipitated
  4. filtrationare filtered away
  5. customThe filtered is evaporated to dryness
  6. extractionextracted with Et2O
  7. additionthe aqueous phase is treated with 40 ml NaOH conc.
  8. extractionextracted with Et2O (4×50 ml)
  9. customThe ethere-phase, dried
  10. additionis treated with HCl in Et2 O about 3N
  11. filtrationthe precipitate is collected by filtration
  12. customcrystallized from EtOH giving 5.98 g (42%) of the wanted compound

Sources & evidence

ORD record
ord-9c5d21b2958d4cd99eb87f76a021a55d
Source dataset
uspto-grants-1998_08
Patent number
US05798362

Reaction notes

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