N,N-Diethylethylenediamine → N1,N1-Diethyl-N2-(5-phenoxy-2-pyridinyl)-1,2-ethanediamine
Reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[CH2:15]([N:17]([CH2:21][CH3:22])[CH2:18][CH2:19][NH2:20])[CH3:16]>>[CH2:15]([N:17]([CH2:21][CH3:22])[CH2:18][CH2:19][NH:20][C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1)[CH3:16]Participants
3
Procedure
To a solution of 3.9 g 6-chloro-3-phenoxypyridine in 5 ml n-butnaol, is added 22 g β-diethylaminoethylamine and the solution is refluxed for 72 hours. The mixture is concentrated at reduced pressure. The residue is shaken with 500 ml dichloromethane and excess dilute sodium hydroxide. The organic phase is separated, dried and distilled; bp 115°-145° C./0.1 mm. The oil is chromatographed over 150 g basic alumina (Woelm, grade I) in toluene and eluted with 0.4% MeOH in toluene. The fractions containing pure product are combined, concentrated and distilled to give 6-(β-diethylaminoethylamino)-3-phenoxypyridine; bp 143°-145° C./0.1 mm.
Workup
- temperaturethe solution is refluxed for 72 hours
- concentrationThe mixture is concentrated at reduced pressure