Reacción #5369

Ecuación de reacción

isopropanol

N,O-dimethylhydroxylamine hydrochloride

sodium bicarbonate

N-(3-bromopropyl)phthalimide

→

N-(3-chloropropyl)phthalimide

Rendimiento 46.1%

Disolventes

triethylamine

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture was refluxed for 33 hours
2. 2
   Extracciónextracted with chloroform
3. 3
   OtroThe organic layer was separated
4. 4
   Lavadowas washed with water
5. 5
   Secadodried over magnesium sulfate
6. 6
   workup.DISTILLATIONChloroform was distilled off
7. 7
   Otrothe residue was purified by column chromatography on silica gel

Procedimiento

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.

Fuente