Hydrochloric Acid → 1-Piperazinebutanamine, 4-(1,2-benzisothiazol-3-yl)-

HRID 1252692Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1252692
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][CH2:19][N:20]3C(=O)C4=CC=CC=C4C3=O)[CH2:12][CH2:11]2)=[N:2]1.O.NN.Cl>CO>[NH2:20][CH2:19][CH2:18][CH2:17][CH2:16][N:13]1[CH2:14][CH2:15][N:10]([C:3]2[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[S:1][N:2]=2)[CH2:11][CH2:12]1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 10093606N-[4-{4-(1,2-benzisothiazol-3-yl)-1-piperazinyl}butyl]phthalimide

Produkt 1

HCID 105654621-Piperazinebutanamine, 4-(1,2-benzisothiazol-3-yl)-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of N-[4-{4-(1,2-benzisothiazol-3-yl)-1-piperazinyl}butyl]phthalimide (1 g; 2.38 mmol), hydrazine hydrate (0.2 g; 3.57 mmol) and methanol (10 ml) was refluxed for 2.5 hours. After cooling, the reaction mixture was combined with a 10% aqueous hydrochloric acid solution (20 ml) and stirred. The precipitated crystals were removed by filtration, and the filtrate was neutralized with a 10% sodium hydroxide solution and extracted with chloroform. The organic layer was washed with a saturated sodium chloride solution and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography to give the objective compound as an oily substance. IR νmaxfilm (cm-1): 3360, 3280, 3070, 1590, 1560, 1490.

Aufarbeitung

  1. temperaturewas refluxed for 2.5 hours
  2. temperatureAfter cooling
  3. customThe precipitated crystals were removed by filtration
  4. extractionextracted with chloroform
  5. washThe organic layer was washed with a saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified by silica gel column chromatography
  9. customto give the objective compound as an oily substance

Quellen und Nachweise

ORD-Eintrag
ord-a1c5a96f227c4464abd4d1b44211b5f3
Quelldatensatz
uspto-grants-1988_05
Patentnummer
US04745117

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