# US 11,306,109 B2 · Method for preparing silicon-containing heterocycles > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,306,109 B2 - Document ID: US11306109B2 - Status: Granted - Kind: B2 - Application number: 16/745,609 - Filed: 2020-01-17 - Published: 2020-05-14 - Granted: 2022-04-19 - Earliest claimed: 2017-07-21 - Assignees: Henkel AG & Co. KGaA - Applicants: Henkel AG & Co. KGaA - Inventors: Jan-Erik Damke; Johann Klein; Esteban Mejia; Rok Brisar - Web page: https://patentgrep.com/patent/US11306109B2 ## CPC - C07F 7/1876: {by reactions involving the formation of Si-C linkages} - C07F 7/1892: {by reactions not provided for in C07F7/1876 - C07F7/1888} - C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22) ## Abstract The present invention relates to a method for preparing silicon-containing heterocycles of the general formula (I) wherein R1 is hydrogen; R2 and R3 are same or different and are, independently from one another, selected from a linear or branched, substituted or unsubstituted C1-C20 alkyl or C6-C18 aryl residue which may be interrupted by at least one heteroatom; R4 is selected from a linear or branched C1-C20 alkylene residue which may be interrupted by at least one heteroatom; R5 and R6 are same or different and are, independently from one another, selected from the group consisting of hydrogen, a linear or branched, substituted or unsubstituted C1-C20 alkyl or C6-C18 aryl which may be interrupted by at least one heteroatom, and a C4-C8 cycloalkyl, or R5 and R6 may form a ring, a 4- to 8-membered alkyl ring; and n is 0, 1 or 2, 2, said method comprising a one-step reaction of at least one epoxide compound of the general formula (II) and at least one aminoalkoxysilane having a primary amino group in the presence of a catalyst wherein R5 and R6 are the same as defined for the general formula (I) above; as well as the use of the silicon-containing heterocycles of the general formula (I). ## Claims ### Claim 1 A method for preparing a silicon-containing heterocycle of the general formula (I) wherein R1 is hydrogen; R2 and R3 are same or different and are, independently from one another, selected from a linear or branched, substituted or unsubstituted C1-C20 alkyl or C6-C18 aryl residue which may be interrupted by at least one heteroatom; R4 is selected from a linear or branched, substituted or unsubstituted C1-C20 alkylene residue which may be interrupted by at least one heteroatom; R5 and R6 are same or different and are, independently from one another, selected from the group consisting of hydrogen, a linear or branched, substituted or unsubstituted C1-C20 alkyl or C6-C18 aryl which may be interrupted by at least one heteroatom, and a C4-C8 cycloalkyl, or R5 and R6 may form a ring, a 4- to 8-membered alkyl ring; and n is 0, 1 or 2, said method comprising: providing at least one epoxide compound of the general formula (II) wherein R5 and R6 are the same as defined for the general formula (I) above; providing at least one aminoalkoxysilane having a primary amino group; providing a catalyst, wherein the catalyst comprises a Lewis acid selected from the group consisting of calcium bistrifluoroacetate, calcium bisacetate, calcium bispivalate, calcium bisisobutyrane, calcium bispropionate, calcium acetate, calcium benzoate, calcium cyclohexanecarboxylate, calcium 2,2-difluoroacetate, calcium 2-fluoroacetate, calcium 2-chloroacetate, calcium methyl carbonate, magnesium bistrifluoroacetate, magnesium bisacetate, magnesium bispivalate, magnesium bisisobutyrane, magnesium bispropionate, magnesium acetate, magnesium benzoate, magnesium cyclohexanecarboxylate, magnesium 2,2-difluoroacetate, magnesium 2-fluoroacetate, magnesium 2-chloroacetate, and magnesium methyl carbonate; combining the at least one epoxide compound, the at least one aminoalkoxysilane and the catalyst to form a mixture; and exposing the mixture to conditions suitable to react the at least one epoxide compound with the at least one aminoalkoxysilane in the presence of the catalyst to form the silicon-containing heterocycle of general formula (I). ### Claim 2 (depends on 1) The method according to claim 1, wherein the at least one epoxide is added in a stoichiometric excess ranging from 1% to 100% with respect to the amino groups of the aminoalkoxysilane(s). ### Claim 3 (depends on 1) The method according to claim 1, wherein the aminoalkoxysilane has the general formula (III) wherein R1 to R4 are the same as defined for the general formula (I); and n is 0, 1, 2 or 3. ### Claim 4 (depends on 1) The method according to claim 1, wherein n in the general formula (I) is 2. ### Claim 5 (depends on 1) The method according to claim 1, wherein R3 is selected from a C1-C8 alkyl residue. ### Claim 6 (depends on 1) The method according to claim 1, wherein R4 is selected from a C1-C8 alkylene residue. ### Claim 7 (depends on 1) The method according to claim 1, wherein R5 is selected from C1-C8 alkyl residue and R6 is selected from hydrogen, C1-C8 alkyl residue or a phenyl residue. ### Claim 8 (depends on 1) The method according to claim 1, wherein the reaction is carried out at a temperature in the range of from −100 to 50° C. ### Claim 9 (depends on 1) The method according to claim 1, wherein the mixture comprises up to 10 mol-% catalyst, relative to the mol-% of the amine functionality of the aminoalkoxysilane. ### Claim 10 (depends on 1) The method according to claim 1, wherein the mixture further comprises at least one solvent selected from the group consisting of toluene, acetonitrile, tetrahydrofuran, ethylene glycol, diethyl ether, dimethyl ether, benzene, ethyl acetate, isopropanol, propanol, ethanol, methanol, chloroform, chloromethane, dichloromethane, pentane, hexane, heptane, cyclohexane, isooctane, toluene, xylene, dioxane, butyl acetate, acetonitrile, and dimethylformamide mixtures thereof. ### Claim 11 (depends on 1) The method according to claim 1, further comprising the step of purifying the silicon-containing heterocycle of general formula (I). ### Claim 12 (depends on 1) The method according to claim 1, further comprising the steps of purifying and separating the silicon-containing heterocycle of general formula (I) into a product.