Morpholine → 4-(2-Chloropyridin-4-yl)morpholine

Reaktionsgleichung

C(N(CC)CC)C.[Cl:8][C:9]1[CH:14]=[C:13](Cl)[CH:12]=[CH:11][N:10]=1.[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1>>[Cl:8][C:9]1[CH:14]=[C:13]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[CH:12]=[CH:11][N:10]=1

Komponenten

Edukt 3

HCID 8083Morpholine

HCID 8471Triethylamine

HCID 335152,4-Dichloropyridine

Produkt 1

HCID 532174144-(2-Chloropyridin-4-yl)morpholine

Versuchsvorschrift

To a solution of triethylamine (1.0 equiv.) and 2,4-dichloropyridine (1.0 equiv.) at RT was added morpholine (1.0 equiv) in one portion, the resulting mixture was then stirred at RT for 45 hr. LCMS analysis indicated the formation of the desired product (M+H=199, Rt=0.29 min, major) and the undesired isomer (M+H=199, Rt=0.33 min, minor). The reaction mixture was concentrated in vacuo and purified via ISCO to yield 4-(2-chloropyridin-4-yl)morpholine as a light brown solid (28%). LCMS (m/z) (M+H)=299.0, Rt=0.29 min. 1H NMR (400 MHz, <cdcl3>) δ ppm 3.18-3.37 (m, 4H) 3.72-3.91 (m, 4H) 6.51-6.61 (m, 1H) 6.61-6.69 (m, 1H) 8.05 (d, J=6.26 Hz, 1H)