DIBENZOOXEPINE AND DIBENZOTHIEPINE DERIVATIVES

Compounds of the general formula in which X is an oxygen or sulphur atom, R is a hydrogen or halogen atom or an alkyl or alkoxy radical and A is a tertiary amino group, and their acid addition salts are prepared by reacting a compound of the general formula in which X and R are as defined above and Y represents a halogen atom or a sulphonic acid ester group of the general formula -O-SO2-R1 in which R1 is an alkyl or aryl radical, with a compound of the formula HA, in which A is as defined above, the product being converted, if desired, into an acid addition salt. The invention also comprises the compounds of formula (1) above in which X is oxygen or sulphur, R is hydrogen, and A is the 4-(2-hydroxyethyl)-piperidyl or the 4 - (2 - hydroxyethyl) - piperavinyl-(1) radical. The compounds of formula (3) above are stated to be novel and may be prepared by reacting ketones of the general formula in which R and X are as defined above, with Grignard compounds of the general formula Hal-CH2-CH2-CH2-OR1, in which Hal is a halogen atom and R1 is a methyl, tert-butyl or benzyl radical, to give compounds of the general formula The compounds of formula (4) may then be converted to the compounds of formula (3) in the following ways: (a) when R1 is methyl, tert-butyl or benzyl the compounds may be boiled with aqueous HBr to give products of formula (3) in which Y is a bromine atom; (b) when R1 is a methyl or benzyl radical the compounds may be boiled with acetyl chloride in benzene or with alcoholic HCl to give a compound of general formula which is then treated with boiling HBr to give compounds of formula (3) in which Y is a bromine atom; (c) when R1 is a tert-butyl radical the compounds may be boiled with alcoholic HCl to give a compound of general formula which is then reacted with thionyl chloride to give compounds of formula (3) in which Y is a chlorine atom. Examples are given. In Example 1 a Grignard compound is prepared from 1 - benzyloxy - 3 - chloropropane and magnesium in ether in the presence of methyl iodide. In Example 5 a Grignard compound is produced from (3-chloropropyl) tert-butyl ether and magnesium in ether; the (3-chloropropyl) tert-butyl ether is obtained by reacting isobutylene with 1 - chloropropan - 3 - ol in the presence of concentrated sulphuric acid. In Example 7, the starting material of formula (3) in which X is oxygen, R is