Patent GB-1204520-A (GB)
Title: beta-DIALKYLAMINOALKYLENE ETHERS, PROCESS FOR PREPARING SAME AND COMPOSITIONS CONTAINING SAME
IPC: C07C323/25
Filed: 1967-12-28
Abstract: 1,204,520. Dialkylaminoalkylene ethers. S.C.M. CORP. 28 Dec., 1967 [9 Jan., 1967; 30 Jan., 1967], No. 58968/67. Heading C2C. [Also in Divisions A5 and C4] The invention relates to compounds of a general formula where Y is terpenoid or a non-terpenoid substituted or unsubstituted saturated, or substituted or unsubstituted unsaturated aliphatic or cyclo-aliphatic group; or substituted or unsubstitutd monoaryl, alkaryl or aralkyl groups, R 3  is C 1 -C 6  alkylene, R 1  and R 2  are like or dissimilar C 1 -C 6  alkyls, "n" is an integer of from 1 to 3, X is sulphur or oxygen, and when "n" is one, X is sulphur and when "n" is greater than one, X represents at least one oxygen atom, and with the proviso that when Y is monoterpenyl than n is 2 or 3. When Y is non-terpenoid, e.g. a saturated acyclic aliphatic group, an unsaturated acyclic aliphatic group, a cyclo-aliphatic group or an aryl group and "n" is 1 and X is sulphur, R 3  may be ethylene and R 1  and R 2  ethyl or the compounds may have the formula where R 4  is C 1 -C 6  alkylene and "n" is 1 and X is oxygen or sulphur when "n" is 1 and R 3  is ethylene and R 1  and R 2  ethyl. When Y is terpenoid it may be terpenyl, acyclic terpenyl, geranyl, linalyl, monocyclic terpenyl, carvyl, terpinyl, bicyclic terpenyl, verbenyl, pinocarvyl, sesquiterpenyl or farnesyl and R 3  ethylene and R 1  and R 2  ethyl, "n" is 1 and X sulphur or compounds may have the formula where T is terpenyl or sesquiterpenyl, R 4  is C 1 -C 6  alkylene and "n" is 1 or 2. Compounds of Formula I may be prepared by: (a) forming a reaction mixture comprising a dispersion of (1) a compound of the formulaY-A, where A is XH, X-R-XH, X-R-X-R-XH, Z, X-R-Z, X-R-X-R-Z, and X and Y have the same meaning as above, Z represents a halogen atom having an atomic number of at least 17, and R represents a lower alkylene group of 1 to 3 carbon atoms, and (2) a di-lower alkylamine compound of the formula BN(R 4 )(R 2 ), where B is H, HX-R, HX-R-X-R, Z-R, Z-R-X-R, and where X, Z and R have the meanings abovedescribed, and R 1  and R 2  represent lower alkyl groups of 1 to 3 carbon atoms, and (3) a liquid vehicle, substantially inert toward the above reactants and compound of Formula I, and (b) maintaining said reaction mixture under agitation at a temperature between about 30 and about 160 C. until said beta-di-lower alkyl-amino-lower-alkylene ether is formed, and (c) thereafter separating said ether from the resulting mixture. Compounds of the formula in which T is terpenyl or sesquiterpenyl group, are prepared by reacting a terpene mercaptan, with a dialkylaminohaloalkane hydrohalide in the presence of an aqueous solution of an alkali metal hydroxide at a temperature in the range of from about 50 to about 90 C. to produce the dialkylaminoalkyl thioether of the terpene. Compounds of the formula are prepared by reacting a compound of the formula T-X-R-XH (where T and R are as above-described, X is sulphur or oxygen and one X represents an oxygen atom) with a betadialkylaminochloroalkane hydrochloride in stoichiometric amounts in the presence of a base such as, for example, an alkali metal hydroxide at a temperature between 50 and 90 C. Compounds of the formula are prepared by reacting a mercaptan of Y with a dialkylaminohaloalkane-hydrohalide of the formula (where Z is a halogen, preferably chloride or bromine), in the presence of a base. Compounds of the formula are prepared by reacting a compound of the formula Y-X-R-XH with a compound falling within the scope of Formula VII (where Y is as hereinbefore described, R is lower alkylene, X is sulphur or oxygen but X represents at least one oxygen atom) in the presence of a base. Among many examples given are the thioethers of beta-diethylamino-ethyl, geranyl, -carvyl, -3-pinanyl, -1- (8-mercapto-menthanyl), -1-octyl, -t-dodecyl, -phenyl, -2-isobornoxythyl, and the ethers of beta-diethylamino ethoxy ethyl-geranyl, -isobornyl, -1-menthanyl, and 2-propyl isobornyl.