Reaktion #1277976

Reaktionsgleichung

N-tert-Butyl-4-(5,6,7,8-tetrahydro-imidazo[1,5-a]pyridin-8-yl)-benzamide hydrochloride

thionyl chloride

→

title compound

(rac)-4-(5,6,7,8-tetrahydro-imidazo[1,5-a]pyridin-8-yl)-benzonitrile

Lösungsmittel

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturunder reflux for 7 hours
2. 2
   Sonstigeevaporated
3. 3
   workup.ADDITIONmixed with saturated aqueous sodium bicarbonate solution
4. 4
   SonstigeThe organic phase is separated off
5. 5
   Extraktionthe aqueous phase is extracted with dichloromethane (2×)
6. 6
   TrocknenThe combined organic phases are dried with sodium sulphate
7. 7
   Sonstigeevaporated
8. 8
   Filtrationfiltered
9. 9
   Sonstigedried

Vorschrift

A solution of 1.74 mmol of N-tert-Butyl-4-(5,6,7,8-tetrahydro-imidazo[1,5-a]pyridin-8-yl)-benzamide hydrochloride and 1.4 ml of thionyl chloride in 30 ml of chloroform is stirred under reflux for 7 hours. The reaction mixture is cooled to room temperature and evaporated. The residue is taken up in dichloromethane and mixed with saturated aqueous sodium bicarbonate solution. The organic phase is separated off and the aqueous phase is extracted with dichloromethane (2×). The combined organic phases are dried with sodium sulphate and evaporated. Following flash chromatography (SiO2 60F) of the residue, the resulting solid is stirred in 1:1 diethyl ether/tert-butyl methyl ether, filtered and dried. The title compound is obtained as a cream-colored solid. Rf=0.37 (toluene:methanol=85:15); Rt=4.88

Quelle