GB683977A - Improvements in and relating to tertiary amino alkenes - Google Patents

Abstract

The invention comprises amines of the formula <FORM:0683977/IV (b)/1> where x is 2-7 and R1 and R2 are the same or different alkyl groups of 1-4 carbon atoms or else NR1R2 is a diethanolamino, morpholino, pyrrolidino or piperidino group; also salts of these amines. The compounds are prepared by reacting the corresponding halogen compounds with HNR1R2 (cf. Specification 683,950) or by the dehydration of the corresponding carbinols; these starting materials are described in Specifications 682,160 and 683,978. Examples describe the preparation of compounds where x is 2, 3, 4 or 7 and NR1R2 is dimethylamino, diethylamino, diethanolamino, piperidino, morpholino and pyrrolidino. The oxalates and hydrochlorides are mentioned. The following halides are prepared by dehydration of the tertiary alcohols: 5-bromo-1 : 1-di-21-thienyl-1-pentene, 6-bromo-1 : 1-di-21 - thienyl - 1 - hexene, 9 - bromo - 1 : 1 - di - 21 - thienyl-1-nonene and 4-chloro-1 : 1-di-21-thienyl-1-butene. The Provisional Specification describes the preparation by the above method of aminoalkenes of the formula <FORM:0683977/IV (b)/2> where R1 and R2 are identical aryl, thienyl or pyridyl groups, n is 3-11 and R3 and R4 are alkyl or form a morpholine, pyrrolidine or piperidine ring. These are made by reacting chloro-, bromo- or iodo-esters Hal-(CH2)n-COOR with organometallic compounds to give halocarbinols R1R2C(OH)-(CH2)n-Hal, dehydrating the latter to haloalkenes R1R2C: CH-(CH2)n-1-Hal, followed by reaction with the appropriate secondary amine. Examples are given of the preparation of 6-bromo-1 : 1-diphenylhexanol, 6-bromo-1 : 1-diphenylhexene and 6-piperidino-1 : 1-diphenylhexene.