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Potassium Iodide → 3-{1-[Phenethyl]-4-piperidinyl}-1,2-benzisothiazole hydrobromide

HRID 1248403
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1248403
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[S:9][N:8]=2)[CH2:3][CH2:2]1.[CH2:16]([Br:24])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>O.CN(C)C=O>[BrH:24].[CH2:16]([N:1]1[CH2:2][CH2:3][CH:4]([C:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[S:9][N:8]=2)[CH2:5][CH2:6]1)[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1
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Komponenten

7

Edukt 4

HCID 4875Potassium IodideHCID 7666Phenethyl bromideHCID 11430Potassium CarbonateHCID 133240934-(3-Benzisothiazolyl) piperidine

Produkt 1

HCID 202557573-{1-[Phenethyl]-4-piperidinyl}-1,2-benzisothiazole hydrobromide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A stirred mixture of 5.0 g of 3-(4-piperidinyl)-1,2-benzisothiazole, 4.60 g of phenethyl bromide, 7.95 g of potassium carbonate, 0.25 g of potassium iodide and 90 ml of dimethylformamide was heated at 60° for 20 hrs and stirred for 21/2 days at ambient temperature. The reaction mixture was poured into water and extracted with ethyl acetate. The organic extracts were dried over anhydrous magnesium sulfate and the solvent was removed in vacuo to yield an oil. The oil was purified by elution column chromatography [silica gel (20:1); using 1% methanol in dichloromethane]. The eluate was evaporated and the residue was dissolved in ether and a saturated hydrogen bromide/ether solution was added dropwise to precipitate the salt. The salt was recrystallized from ether-ethanol 3.0 g (32%) of product, mp 233°-235°.

Aufarbeitung

  1. temperaturewas heated at 60° for 20 hrs
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic extracts were dried over anhydrous magnesium sulfate
  4. customthe solvent was removed in vacuo
  5. customto yield an oil
  6. customThe oil was purified by elution column chromatography [silica gel (20:1); using 1% methanol in dichloromethane]
  7. customThe eluate was evaporated
  8. dissolutionthe residue was dissolved in ether
  9. additiona saturated hydrogen bromide/ether solution was added dropwise
  10. customto precipitate the salt
  11. customThe salt was recrystallized from ether-ethanol 3.0 g (32%) of product, mp 233°-235°

Quellen und Nachweise

ORD-Eintrag
ord-6fadac015a034970aedf2ba66347c9cc
Quelldatensatz
uspto-grants-1985_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04524074

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