Reaktion #65638

Reaktionsgleichung

NH4Cl

8-chloro-10,11-dihydrodibenz[b,f][1,4]oxazepine

n-butyl lithium

3-chloromethyl-6-bromopyridine

→

title compound

Ausbeute 80.7%

10-[(2-bromo-5-pyridinyl)methyl]-8-chloro-10,11-dihydrodibenz[b,f][1,4]oxazepine

Ausbeute 80.7%

Lösungsmittel

THF

hexane

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITAfter 30 minutes
2. 2
   workup.WAITAfter 30 minutes
3. 3
   Extraktionthe mixture was extracted with ether
4. 4
   ExtraktionThe organic extract
5. 5
   Trocknenwas dried over MgSO4
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe residue was chromatographed over silica gel using 10% ethyl acetate in hexane as eluant

Vorschrift

To a stirred solution of 8-chloro-10,11-dihydrodibenz[b,f][1,4]oxazepine (2 g) in THF (25 mL) at -78° C. was added 1.6 M hexane solution of n-butyl lithium (5.4 mL). After 25 minutes, 3-chloromethyl-6-bromopyridine (1.79 g) in THF (5 mL) was added. After 30 minutes, the temperature was raised to -23° C. After 30 minutes, an excess saturated solution of NH4Cl was added and the mixture was extracted with ether. The organic extract was dried over MgSO4 and concentrated. The residue was chromatographed over silica gel using 10% ethyl acetate in hexane as eluant. Appropriate fractions were pooled to give the title compound (2.8 g) as a thick gum.

Quelle