Reaction #65134

Reaction equation

4-chlorobutyryl chloride

10,11-dihydrodibenzo[b,e][1,4]diazepin-11-one

→

title compound

5- (4-Chlorobutyryl)-10,11-dihydrodibenzo [b,e][1,4]diazepin-11-one

Solvents

acetone

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   Temperatureunder reflux for 8 hours
3. 3
   Otherevaporated
4. 4
   OtherThe residue was purified by chromatography on silica
5. 5
   Otherevaporated
6. 6
   Otherthe residue triturated with hexane/dichloromethane

Procedure

A mixture of 4-chlorobutyryl chloride (3.5 g) and 10,11-dihydrodibenzo[b,e][1,4]diazepin-11-one (4.2 g) (J. Med. Chem., 1963, 6, 767) in acetone (90 ml) was heated under reflux for 8 hours and evaporated. The residue was purified by chromatography on silica using hexane plus 0-100% dichloromethane as eluant. Appropriate fractions were combined and evaporated and the residue triturated with hexane/dichloromethane to give the title compound as a colourless solid, 1.62 g (26%), m.p. 151°-152° C.

Source