process for the production of new chinazolindion compounds and their salts

摘要

1379188 Quinazoline derivatives PARKE DAVIS & CO 20 Aug 1973 [21 Aug 1972] 39326/73 Heading C2 The invention comprises compounds of formula or acid addition salts thereof; wherein RSP1/SP represents -C 2 H 5 , or an n- or iso-propyl group; RSP2/SP represents H or -CH 3 ; n represents 4, 5 or 6; and each of X and Y represents H or -OCH 3 . These compounds may be obtained by reacting an o-aminobenzamide of formula with phosgene. The starting material (B) may be prepared by the following sequence of reactions: 1-(o-alkylthiophenyl piperazine of formula is reacted with a bromonitrile of formula Br-(CH 2 ) n-1 -CN in the presence of K 2 CO 3 and the product reduced with LiAlH 4 followed by hydrolysis to give 1-(aminoalkyl)-4-(o-alkylthiophenyl)piperazine of formula The product D is reacted with an isatoic anhydride of formula to produce an o-aminobenzamide of Formula B. According to another sequence of reactions a benzoic acid derivative of formula is converted to the acid chloride by reaction with thionyl chloride, and the acid chloride is reacted with a compound of Formula (D), and the reaction product is treated with a base to produce an o-nitrobenzamide of formula This compound is reduced to form an amide of Formula (B) The compounds according to the invention are reported to have central nervous system depressant activity.