تفاعل #741704

معادلة التفاعل

thionyl chloride

Ethyl 1-azabicyclo[3.2.1]oct-5-ylcarboxylate

hydrochloric acid

potassium carbonate

ammonia dichloromethane

→

title compound

المردود 76.0%

1-Azabicyclo[3.2.1]oct-5-ylcarboxamide

المردود 76.0%

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةheated
2. 2
   درجة الحرارةunder reflux for 18h
3. 3
   تركيزThe solution was concentrated in vacuo
4. 4
   أخرىto give a white solid, which
5. 5
   درجة الحرارةheated
6. 6
   درجة الحرارةunder reflux for 6h
7. 7
   تركيزThe reaction mixture was concentrated in vacuo
8. 8
   أخرىto leave a red semi-solid, which
9. 9
   درجة الحرارةcooled in an ice bath
10. 10
    أخرىThe organic layer was separated
11. 11
    استخلاصthe aqueous was extracted with chloroform (3×70 ml)
12. 12
    تجفيفdried (Na2SO4)
13. 13
    تركيزconcentrated in vacuo

الإجراء التجريبي

Ethyl 1-azabicyclo[3.2.1]oct-5-ylcarboxylate (E7, Example 7 hereinafter, 9.6 g, 0.053 mole) was treated with 8M hydrochloric acid (130 ml) and heated under reflux for 18h. The solution was concentrated in vacuo to give a white solid, which was treated with thionyl chloride (80 ml) and heated under reflux for 6h. The reaction mixture was concentrated in vacuo to leave a red semi-solid, which was suspended in dichloromethane (120 ml), cooled in an ice bath and treated with an excess of ammonia/dichloromethane solution. The mixture was stirred at room temperature for 1h, then treated with saturated potassium carbonate solution. The organic layer was separated and the aqueous was extracted with chloroform (3×70 ml). All the organics were combined, then dried (Na2SO4) and concentrated in vacuo to give the title compound (D20) as a brown solid (6.2 g, 76%), which was used without further purification.

المصدر