Hydrochloric Acid → 1-(1,4-Benzodioxan-2-ylcarbonyl)piperazine hydrochloride

HRID 354839

Reaktionsgleichung

Reaktionsgleichung von HRID 354839
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C([O-])(=O)C.[Na+].Cl.[O:13]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[O:16][CH2:15][CH:14]1[C:23]([Cl:25])=[O:24].[OH-].[Na+]>O.CC(C)=O>[ClH:25].[O:13]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[O:16][CH2:15][CH:14]1[C:23]([N:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1)=[O:24]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 4837PiperazineHCID 14798Sodium Hydroxide3×HCID 517045Sodium AcetateHCID 27354472,3-Dihydro-1,4-benzodioxin-2-carbonyl chloride

Produkt 1

HCID 28224341-(1,4-Benzodioxan-2-ylcarbonyl)piperazine hydrochlorideAusbeute 12,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

A suspension of piperazine (11.88 g.) and sodium acetate (20.30 g.) in a mixture of water (70 ml.) and acetone (95 ml.) was stirred at 10°-15° C., then concentrated hydrochloric acid was added (about 35 ml.) until the pH of the solution reached 1.5. 1,4-Benzodioxan-2-carbonyl chloride (31.0 g.) and sodium hydroxide (5 N, about 45 ml.) were then added portionwise while maintaining the temperature at 10°-15° C., the sodium hydroxide maintaining the pH at 1.7-2.2. After the addition was complete, the pH was adjusted to 2.0 by the addition of sodium hydroxide, the suspension was stirred for a further 30 minutes. Water was then added until a homogeneous solution resulted, the acetone removed in vacuo, and the aqueous phase was basified to pH 8-9 with sodium hydroxide (5 N), re-extracted with chloroform (3×200 ml.) and the extracts washed with water, dried (MgSO4) and evaporated in vacuo. The oily residue was dissolved in ethyl acetate, treated with ethereal hydrogen chloride, evaporated in vacuo and the solid residue triturated with ether, followed by recrystallization from methanol to give N-(1,4-benzodioxan-2-carbonyl)-piperazine hydrochloride (4.85 g.), M.P. 265°-267° C.

Aufarbeitung

  1. temperaturewhile maintaining the temperature at 10°-15° C.
  2. additionAfter the addition
  3. stirringthe suspension was stirred for a further 30 minutes
  4. customresulted
  5. customthe acetone removed in vacuo
  6. extractionre-extracted with chloroform (3×200 ml.)
  7. washthe extracts washed with water
  8. dry with materialdried (MgSO4)
  9. customevaporated in vacuo
  10. dissolutionThe oily residue was dissolved in ethyl acetate
  11. additiontreated with ethereal hydrogen chloride
  12. customevaporated in vacuo
  13. customthe solid residue triturated with ether
  14. customfollowed by recrystallization from methanol

Quellen und Nachweise

ORD-Eintrag
ord-ad716962594649ddb4f9fab4437c3eb8
Quelldatensatz
uspto-grants-1983_03
Patentnummer
US04377581

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