A series of compounds of 1,5-benzodiazepines and its chloroacetylated derivatives have been synthesized and its physicochemical parameters were evaluated in order to determine the potency of the compounds for good CNS activity. This solvent free reaction mediated by glacial acetic acid was found to be very efficient with high yield. The structures were confirmed on the basis of TLC, IR and 1HNMR and CHN elemental studies. The log P values of two of the compounds shows that compounds have the potential to be CNS active and all other parameters like non-value, non-value, n-violations and number of rotatable bonds also lies in the ranges that are required for blood brain barrier penetration. This synthesis provides a new hope that the free chloro group in this structure can be utilized for further substitution of various heterocyclic rings which possess potent CNS activity.