تفاعل #2383511

معادلة التفاعل

hydrogen chloride

8-chloro-6-(2-fluorophenyl)-2H,4H-pyrrolo[3,4-d][2]benzazepine

potassium t-butoxide

dimethylaminopropyl chloride

→

8-Chloro-2-[3-(dimethylamino)propyl]-6-(2-fluorophenyl)-2H,4H-pyrrolo[3,4-d][2]benzazepine dihydrochloride

المذيبات

dimethylformamide

water

toluene

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwas cooled to 0°
2. 2
   workup.STIRRINGstirred for 4 hr
3. 3
   استخلاصextracted with methylene chloride
4. 4
   غسيلThe methylene chloride solution was washed with water
5. 5
   تجفيفdried over anhydrous sodium sulfate
6. 6
   تركيزconcentrated at reduced pressure
7. 7
   أخرىPurification of the residue by column chromatography (silica gel, 25 g; eluents, 4:1 ration of methylene chloride:ether followed by 1:2:7 ratio of methanol:ether:methylene chloride)
8. 8
   أخرىgave a colorless oil
9. 9
   تركيزthe solution was concentrated at reduced pressure
10. 10
    أخرىCrystallization of the residue
11. 11
    workup.ADDITIONfrom a mixture of isopropanol and ether
12. 12
    أخرىgave an orange solid, mp 258°-260°

الإجراء التجريبي

In one portion 1.5 g (4.8 mmol) of 8-chloro-6-(2-fluorophenyl)-2H,4H-pyrrolo[3,4-d][2]benzazepine was added to a solution of 0.6 g (5.3 mmol) of potassium t-butoxide in 25 ml of dimethylformamide which was cooled to 0°. After stirring for 15 min, 5.2 ml (10.4 mmol) of a 2 M toluene solution of dimethylaminopropyl chloride was added. The mixture was warmed to room temperature and stirred for 4 hr. The mixture was diluted with water and extracted with methylene chloride. The methylene chloride solution was washed with water, dried over anhydrous sodium sulfate and concentrated at reduced pressure. Purification of the residue by column chromatography (silica gel, 25 g; eluents, 4:1 ration of methylene chloride:ether followed by 1:2:7 ratio of methanol:ether:methylene chloride) gave a colorless oil. The oil was dissolved in an excess of methanolic hydrogen chloride and the solution was concentrated at reduced pressure. Crystallization of the residue from a mixture of isopropanol and ether gave an orange solid, mp 258°-260°.

المصدر