반응 #72738

반응 방정식

(−)-5-(2-bromopyrid-5-yl)-1-azabicyclo[3.2.1]octane hydrobromide

potassium cyanide

sodium carbonate

→

expected product

수율 76.9%

(−)-(1-Azabicyclo[3.2.1]oct-5-yl)pyridine-2-carbonitrile

수율 76.9%

용매

dimethylformamide

반응 조건

후처리

1. 1
   추출The aqueous phase is extracted with chloroform
2. 2
   건조the combined organic phases are dried over sodium sulfate
3. 3
   여과filtered
4. 4
   농축concentrated under reduced pressure
5. 5
   기타The residue is purified by chromatography on a column of silica gel
6. 6
   세척eluting with a mixture of chloroform, methanol and aqueous ammonia in 95/5/0.5 proportions

실험 절차

1.5 g (4.3 mmol) of (−)-5-(2-bromopyrid-5-yl)-1-azabicyclo[3.2.1]octane hydrobromide (prepared according to the method described in step 1.2 of Example 1), dissolved in 12 ml of dimethylformamide, 0.42 g (6.46 mmol) of potassium cyanide and 5 g (4.3 mmol) of tetrakis(triphenylphosphine)palladium are successively introduced into a 25 ml reactor. The mixture is then heated at 90° C. for 3 hours and then neutralized with saturated aqueous sodium carbonate solution. The aqueous phase is extracted with chloroform and the combined organic phases are dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue is purified by chromatography on a column of silica gel, eluting with a mixture of chloroform, methanol and aqueous ammonia in 95/5/0.5 proportions. 0.705 g of expected product is thus obtained in the form of an amorphous solid.

출처