PL86974B1 - Basic ethers[au6018473a] - Google Patents

Abstract

1377350 Basic ethers CHEMIE LINZ AG 6 Sept 1973 [11 Sept 1972] 42063/73 Heading C2C Compounds of the general formula (R = C 1-4 alkyl; R 1 = H, C 1-4 alkyl, allyl, PhCH 2 ; R 2 =C 2-6 alkenyl, ar(C 2-4 alkenyl) optionally C 1-4 alkoxy substituted, C 2-6 haloalkenyl, C 2-3 alkynyl, C 3-6 cycloalkyl, cycloalkylidenemethyl containing up to seven carbon atoms; R 3 =H, Me) and their salts are prepared by reacting a compound of the formula (X=NHR 4 , N=CHR 5 ; R 4 =C 1-4 alkyl, allyl, PhCH 2 , acyl; R 5 = aryl, optionally substituted) with R 2 CH 2 Hal (Hal=halogen) and removing any CHR 5 or acyl group present in the product, optionally followed by introduction of an R 1 substituent and/or salt formation. The starting materials are prepared by standard methods. The above compounds are analgesics, and may be administered in the form of pharmaceutical preparations containing them in association with a carrier. [GB1377350A]

Claims (10)

1. Claims 1. A process for the preparation of new basic ethers of the general formula, in which R is an alkyl radical of at most 4 carbon atoms, Rx is a lower alkyl radical, allyl or benzyl radical, R2 is an alkenyl, aralkenyl, haloalkenyl, alkynyl radical -cycloalkyl or cycloalkylidenemethyl, aR3 represents a hydrogen atom or a methyl radical, and their acid addition salts, such as the basic ether of the general formula II, in which R and R3 are as defined above, and R <is the lower radical an alkyl, allyl or benzyl radical, is reacted with a halogen compound of the general formula, in which Ra is as defined above and Hal is a halogen atom, and the base obtained is optionally converted into an acid addition salt or the salt obtained is liberated . 2. The method according to claim 3. The process of claim 1, characterized in that the reactions are carried out in the presence of acid-binding agents and at elevated temperature, 3. 3. A process for the preparation of new basic ethers of general formula I, in which R is an alkyl radical of at most 4 carbon atoms. 4. R * is a hydrogen atom, Ra is an alkenyl, aralkenyi, haloalkenyl, alkynyl, cycloalkyl or cycloalkylidenemethyl radical, and R3 is a hydrogen atom or a methyl radical, and their acid addition salts, Zn, and m4, e, n, and y. with a basic ether of general formula II in the presence of a base or an alkali metal salt with a basic ether of formula II, wherein in formula II the symbols R s, Ra have the meanings given above, aR | represents an acyl radical, is reacted with a halogen compound of formula III, in which Ra is as defined above and Hal is a halogen atom, then the acyl radical is hydrolytically cleaved in the obtained compound and the base obtained is optionally converted into an acid addition salt or with of the obtained salt is released by the principle of the method according to claim 3, characterized in that the alkali metal salt with a basic ether of mtu 2 is prepared by reaction of a basic ether of formula 2, wherein R, R 3 and R 1 is as defined in claim 3 with an alkali metal hydride, is used in an aprotic solvent environment, preferably in the environment of phosphoric acid hexamethiotriamide. 5. The method according to claim 3, with n a m and e n n y m, that a compound of formula 2 is used as a substrate, in which R \ is a trifluoroacetyl group, and this group is cleaved by alkaline hydrolysis, 6., A method for the preparation of new basic ethers of the general formula I, in which R is an alkyl radical of at most 4 carbon atoms, Ri is an alkyl, allyl or benzyl radical, R2 is an alkenyl, aralkenyl, haloalkenyl, alkynyl, cycloalkyl or cycloalkylmethyl radical and R3 represents a hydrogen atom or a methyl radical and acid addition salts thereof, characterized in that a basic ether of general formula II in the presence of a base or an alkali metal salt with a basic ether of formula II, and the symbols Ri R3 in formula II are . The meaning given above, and R'1 is an acyl radical, is reacted with a halogen compound of formula 3, in which R2 is as defined above, and Hal is a halogen atom, and then the acyl radical is hydrolytically cleaved in the resulting compound in the resulting , the secondary amino group, the hydrogen atom is replaced with an alkyl, allyl or benzyl radical and the base obtained is optionally converted into an acid addition salt or the base obtained is liberated from the salt obtained. The process according to claim 6, in the form of an alkali metal salt with a basic ether of formula 2, prepared by reaction of a basic ether of formula 2, wherein R, R 3 and R * i have the meaning given in claim 6, with an alkali metal hydride, is used in an aprotic solvent environment, preferably in an environment of hexamethyl phosphoric triamide. 8. The method according to claim 6, characterized in that the substrate is a compound of formula 2, wherein R * i represents a trifluoroacetic group, and this group is cleaved by alkaline hydrolysis. 9. A process for the preparation of new basic ethers of general formula I, in which R is an alkyl radical of at most 4 carbon atoms, Rx is an allyl radical, Ra is a vinyl radical, and R3 is a hydrogen atom or a methyl radical, and acid addition salts thereof, characterized by the basic ether of formula II, in which R and R &lt; 1 &gt; are as defined, and R1 is hydrogen, is reacted with a halogen of formula III in which R2 is vinyl and Hal is halogen, and the resultant the base is optionally converted into an acid addition salt or the base is liberated from the salt obtained. 10. The method according to p. 9. A process according to claim 9, characterized in that the reactions are carried out in the presence of acid binding agents and at an elevated temperature. 86 974 R, "3 R, Os / CH-CHj-N ^ • OR CH2-Rz Formula R3 R 'XH-CH2- <// ^ xc // \ S \ 0R Formula 2 Hal-CH2-R2 Bteói-J ¦NH, + Hal-CO-Rj- * -NH.CQ.R4 + - N .CORi CH2-R2 + Hal-CH2-Ra - -NH.CHZR2 + R4.CQ0H Scheme Work. Poi; y; df. U *;! RU i -. Akf «cj" '' O-HO PL