Isopropanol → 2-(3-Chloropropyl)-1H-isoindole-1,3(2H)-dione

HRID 5273

Reaktionsgleichung

Reaktionsgleichung von HRID 5273
C(O)(C)C.[ClH:5].CNOC.Br[CH2:11][CH2:12][CH2:13][N:14]1[C:18](=[O:19])[C:17]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]2[C:15]1=[O:24].C(=O)(O)[O-].[Na+]>C(N(CC)CC)C>[Cl:5][CH2:11][CH2:12][CH2:13][N:14]1[C:18](=[O:19])[C:17]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]2[C:15]1=[O:24]

Komponenten

6

Edukt 4

HCID 3776IsopropanolHCID 21611N-3-BromopropylphthalimideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 516892Sodium Bicarbonate

Produkt 1

HCID 2452652-(3-Chloropropyl)-1H-isoindole-1,3(2H)-dioneAusbeute 46,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a suspension of 50 mol of isopropanol containing N,O-dimethylhydroxylamine hydrochloride (3.97 g, 40.0 mmol) was added dropwise 5.56 ml of triethylamine. After 5 minutes, there was added 2.68 g (10.0 mmol) of N-(3-bromopropyl)phthalimide and the mixture was refluxed for 33 hours. This was cooled to room temperature, then poured into 200 ml of saturated aqueous solution of sodium bicarbonate and extracted with chloroform. The organic layer was separated and was washed with water and dried over magnesium sulfate. Chloroform was distilled off and the residue was purified by column chromatography on silica gel. Development with 30% hexane-chloroform resulted in elution of 1.03 g of N-(3-chloropropyl)phthalimide and further development with chloroform resulted in 1.21 g (yield: 53%) of white crystals of N-[3-(N-methoxy-N-methylamino)propyl]-phthalimide.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 33 hours
  2. extractionextracted with chloroform
  3. customThe organic layer was separated
  4. washwas washed with water
  5. dry with materialdried over magnesium sulfate
  6. distillationChloroform was distilled off
  7. customthe residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-a7a6cc20410049fab1aec4b794941182
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05244487

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