3-Fluorobenzodiazepines

#The invention relates to novel 3-fluoro-2,3-dihydro-1H-1,4-benzodiazepin-2-ones.

#Structurally similar compounds which are unsubstituted by a fluorine atom in the 3-position, for example, 1-methyl-5-phenyl-7-chloro-2,3-dihydro-1H-1,4-benzodiazepin-2-one (diazepam) and 3-chlorodiazepam, are known.

#In one composition aspect, this invention relates to 3-fluoro-2,3-dihydro-1H-1,4-benzodiazepin-2-ones of the formula ##STR2## wherein R.sup.1 is H, alkyl or fluorinated alkyl of 1-4 carbon atoms and up to 9 fluorine atoms or cycloalkylalkyl of 4-8 carbon atoms; R.sup.2 is phenyl, monohalophenyl or pyridyl; R.sup.3 is F, Cl, Br or NO.sub.2, and physiologically acceptable acid addition salts thereof.

#Without further elaboration, it is believed that one skilled in the art can, using the preceding description, utilize the present invention to its fullest extent. The following preferred specific embodiments are, therefore, to be construed as merely illustrative, and not limitative of the remainder of the disclosure in any way whatsoever.

#20 ml. of benzene are added, under nitrogen, to a mixture of 0.1 mole of n-butyl lithium in 20 ml. of hexane and 10 g. of diisopropylamine are added dropwise at 0.degree.. A solution of 28.5 g. of 1-methyl-5-phenyl-7-chloro-2,3-dihydro-1H-1,4-benzodiazepin-2-one (diazepam) in 800 ml. of benzene is then added. After stirring for 1 hour at about 20.degree., the mixture is evaporated and the residue is taken up in 300 ml. of THF and a solution of 22 g. ClO.sub.3 F in 60 ml. of THF is added dropwise. After stirring for 2 hours, the mixture is evaporated and worked up in the customary manner. The product is 1-methyl-3-fluoro-5-phenyl-7-chloro-2,3-dihydro-1H-1,4-benzodiazepin-2-one (3-fluorodiazepam), m.p. 152.degree.-154.degree..

#The following are obtained by the method of Example 1 from the corresponding compounds of Formula II (X is H):