تفاعل #5369

معادلة التفاعل

isopropanol

N,O-dimethylhydroxylamine hydrochloride

sodium bicarbonate

N-(3-bromopropyl)phthalimide

→

N-(3-chloropropyl)phthalimide

المردود 46.1%

المذيبات

triethylamine

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe mixture was refluxed for 33 hours
2. 2
   استخلاصextracted with chloroform
3. 3
   أخرىThe organic layer was separated
4. 4
   غسيلwas washed with water
5. 5
   تجفيفdried over magnesium sulfate
6. 6
   workup.DISTILLATIONChloroform was distilled off
7. 7
   أخرىthe residue was purified by column chromatography on silica gel

الإجراء التجريبي

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.

المصدر