Substituted 5h-dibenz [b.f] azepines and processes for their production

摘要

The invention comprises substituted 5H-dibenz[b,f]azepines of the general formula: (wherein Y and Z each represent a hydrogen or halogen atom, one of R1 and R2 represents a methyl group and the other a hydrogen atom, and R3 and R4 represent C1- 4 alkylene radicals bound to each other through an oxygen atom or an alkylimino, hydroxyalkylimino or alkanoyloxyimino group having at most 4 carbon atoms), and the preparation thereof by (1) reaction of a dibenzazepine of the general formula: with a reactive ester of a basic alcohol of the general formula: or (2) reacting a reactive ester of a hydroxy compound of the general formula: with a secondary amine of the general formula: or (3) heating a compound of the general formula: until one molecular proportion of carbon dioxide is split off. The preparation of 5-g -[41-(211-acetoxyethyl)-piperazinyl-11] - b -methylpropyl-5H-dibenz [b,f] azepine by acetylating the corresponding 211-hydroxy compound is also described. The products, which form salts with inorganic or organic acids, have spasmolytic, antiallergic, sedative, anticonvulsive and anti-emetic activity. Chlorides of basic alcohols III are prepared as follows: (a) (when R1=H, R2=CH3] by reacting 1, 3-butyleneglycol with acetyl chloride to form 3-chloro-n-butyl acetate, reacting this with an amine V, and chlorinating the resulting 3-tertiary amino-n-butanol; (b) (when R1=CH3, R2=H) adding hydrogen bromide to b -methallyl chloride in the presence of dibenzoyl peroxide and reacting the resulting g -bromo-b -methylpropyl chloride with an amine V. 5-(g -Chloro-b -methylpropyl)-5H-dibenz [b, f]-azepine is prepared by reacting 5H-dibenz [b,f] azepine with 1-chloro-2-methyl-3-bromopropane in toluene in the presence of sodamide. Reference has been directed by the Comptroller to Specification 914,717.