반응 #218365

반응 방정식

N-Benzylethanolamine

2-Chloroacrylonitrile

water

N-benzylethanolamine

N-benzylethanolamine

Potassium tert-butoxide

→

title compound

수율 65.0%

4-Benzyl-morpholine-2-carbonitrile

수율 65.0%

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   온도A one-litre reactor with mechanical stirring, cooled by an ice bath
2. 2
   기타transferred to a 2 L reactor
3. 3
   기타at 0±2° C
4. 4
   workup.STIRRINGAfter 1 hour post-stirring at 0° C.
5. 5
   기타the mixture was quenched with saturated NaHCO3 (500 mL)
6. 6
   추출The aqueous layer was extracted with diethyl ether (500 mL)
7. 7
   기타Organic layers were dried on MgSO4
8. 8
   기타evaporated to dryness

실험 절차

A one-litre reactor with mechanical stirring, cooled by an ice bath, was charged with N-benzylethanolamine (172.2 g; 1 equiv. available from Aldrich Chemical Company). 2-Chloroacrylonitrile (100 g; 1 equiv. available from Aldrich Chemical Company) was added dropwise over 2 minutes. The temperature was maintained between 23° C. and 29° C. by means of the ice bath and subsequently a water bath at 15° C. N-Benzylethanolamine was still detected on TLC after 4.5 h stirring. After one night stirring at room temperature (water bath), no N-benzylethanolamine was detectable by 1H NMR. The mixture was dissolved in tetrahydrofuran and transferred to a 2 L reactor cooled to −5° C. by ice/NaCl bath. The total volume of tetrahydrofuran was 1.35 L. Potassium tert-butoxide (148 g; 1.1 equiv.) was added by portions in 1 hour, keeping the reaction temperature at 0±2° C. After 1 hour post-stirring at 0° C., the mixture was quenched with saturated NaHCO3 (500 mL). The aqueous layer was extracted with diethyl ether (500 mL). Organic layers were dried on MgSO4 and evaporated to dryness. The title compound (149.8 g; 65%) was obtained after percolation of the 250 g dry residue on 1 kg of SiO2, eluting with the following gradient:

출처