CN116693399A - Preparation method of iodo-N, N, N-trimethyl-cyclohexenyl ammonium salt - Google Patents
Preparation method of iodo-N, N, N-trimethyl-cyclohexenyl ammonium salt Download PDFInfo
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- CN116693399A CN116693399A CN202310609293.2A CN202310609293A CN116693399A CN 116693399 A CN116693399 A CN 116693399A CN 202310609293 A CN202310609293 A CN 202310609293A CN 116693399 A CN116693399 A CN 116693399A
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- China
- Prior art keywords
- trimethyl
- iodo
- preparation
- cyclohexylammonium salt
- methyl iodide
- Prior art date
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- -1 iodo-N, N, N-trimethyl-cyclohexenyl ammonium salt Chemical class 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- 239000002994 raw material Substances 0.000 claims abstract description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 21
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 claims description 15
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- HCKMSHYCAFVSGW-UHFFFAOYSA-N cyclohexyl(trimethyl)azanium Chemical class C[N+](C)(C)C1CCCCC1 HCKMSHYCAFVSGW-UHFFFAOYSA-N 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 3
- 238000004090 dissolution Methods 0.000 claims description 2
- 238000005580 one pot reaction Methods 0.000 claims description 2
- 238000001514 detection method Methods 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 239000012847 fine chemical Substances 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 abstract description 2
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 230000035484 reaction time Effects 0.000 abstract 1
- 230000008569 process Effects 0.000 description 10
- 239000007787 solid Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000007810 chemical reaction solvent Substances 0.000 description 4
- 238000003760 magnetic stirring Methods 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 2
- LHKPZENZOYGYTA-UHFFFAOYSA-N cyclohexen-1-yl(trimethyl)azanium Chemical class C[N+](C)(C)C1=CCCCC1 LHKPZENZOYGYTA-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- HMKDAISOYWVXCJ-UHFFFAOYSA-M cyclohexyl(trimethyl)azanium;iodide Chemical compound [I-].C[N+](C)(C)C1CCCCC1 HMKDAISOYWVXCJ-UHFFFAOYSA-M 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
- C07C209/12—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Abstract
The invention discloses a preparation method of iodo N, N, N-trimethyl cyclohexylammonium salt, which relates to the technical field of fine chemical intermediates. The reaction has the advantages of no need of heating, no need of adding catalyst, short reaction time, simple reaction device and operation, etc., the yield can reach more than or equal to 90%, and the full utilization of raw materials is realized.
Description
Technical Field
The invention relates to the technical field of fine chemical intermediates, in particular to a preparation method of an iodo N, N, N-trimethyl cyclohexylammonium salt.
Background
The iodized N, N, N-trimethyl cyclohexylammonium salt is an important cyclic quaternary ammonium salt, and has good hydrophilicity, emulsifying property, high ion adsorption and permeability and diffusion property due to the unique structure, so that the iodized N, N, N-trimethyl cyclohexylammonium salt can be well applied to the aspects of papermaking, dyes, materials and the like, and meanwhile, the quaternary ammonium salt can also be widely applied to the fields of pesticides, medicines and health. Therefore, the compound has higher application value.
No report on the synthesis of iodo-N, N-trimethylcyclohexenium salts has been found in extensive literature studies, and thus it is necessary to develop a synthetic route for preparing the compound.
Disclosure of Invention
The invention aims to provide a preparation method of iodized N, N, N-trimethyl-cyclohexenyl ammonium salt, which solves the problem that the prior art proposed in the background art does not have a synthetic process route for iodized N, N, N-trimethyl-cyclohexenyl ammonium salt.
In order to achieve the above purpose, the present invention provides the following technical solutions: the method uses N, N-dimethylcyclohexylamine as raw material, methylene dichloride or acetone as solvent, and methyl iodide is added to make substitution reaction so as to obtain the invented product.
The specific reaction process is that N, N-dimethyl cyclohexylamine is dissolved in methylene dichloride or acetone, methyl iodide is dripped under the condition of room temperature, the mixture is stirred for 1 to 2 hours, and the crude product is filtered and dried to obtain N, N, N-trimethyl cyclohexylammonium salt, and the yield is 49 to 90 percent. In the raw materials of the invention, the mol ratio of N, N-dimethyl cyclohexylamine to methyl iodide is 1:1-1.5.
Compared with the prior art, the invention has the beneficial effects that:
1. the method for synthesizing the iodo N, N, N-trimethyl cyclohexylammonium salt has the advantages of simple synthesis line, easily obtained raw materials and high reaction efficiency;
2. the invention adopts N, N-dimethyl cyclohexylamine, methyl iodide, methylene dichloride or acetone as solvent to synthesize the iodo N, N, N-trimethyl cyclohexylammonium salt by a one-pot method, and the synthesis process is simple;
3. the invention adopts organic dissolution as a reaction medium, does not generate acid and alkaline waste liquid, can be carried out under the condition of normal temperature, and has green and environment-friendly synthesis process.
Drawings
FIG. 1 is a nuclear magnetic resonance spectrum of N, N, N-trimethylcyclohexenium iodide prepared in accordance with the present invention;
FIG. 2 is a diagram showing the structure of N, N-dimethylcyclohexylamine;
FIG. 3 is a block diagram of an N, N, N-trimethylcyclohexylammonium iodide salt.
Detailed Description
The present invention is described in detail below by way of specific examples, but the scope of the present invention is not limited thereto. Unless otherwise specified, the experimental methods adopted in the invention are not conventional methods, and all experimental equipment, materials, reagents and the like used in the method can be obtained from commercial sources.
Example 1:
the present example is a process for the preparation of an iodo-N, N, N-trimethylcyclohexylammonium salt with dichloromethane as the reaction solvent, according to the following reaction scheme:
wherein: the molar ratio of N, N-dimethylcyclohexylamine to methyl iodide is 1:1.
The specific experimental process is as follows:
in a 50ml three-necked flask, 1.26g (0.01 mol,97%,1 eq) of N, N-dimethylcyclohexylamine was dissolved in 20ml of methylene chloride, 623. Mu.l (0.01 mol,97%,1 eq) of methyl iodide was added dropwise with magnetic stirring at room temperature, the mixture was refluxed for 1 to 2 hours after the addition, and after the completion of the reaction, the mixture was filtered and dried to obtain a pale yellow solid, and 0.691g of a pale yellow solid N, N, N-trimethylcyclohexylammonium salt product was obtained by recrystallization, GC:97%, separation recovery rate: 49%.
Example 2:
the present example is a process for the preparation of an iodo-N, N, N-trimethylcyclohexylammonium salt with dichloromethane as the reaction solvent, according to the following reaction scheme:
wherein: the molar ratio of N, N-dimethylcyclohexylamine to methyl iodide is 1:1.3.
The specific experimental process is as follows:
in a 50ml three-necked flask, 1.21g (0.01 mol,97%,1 eq) of N, N-dimethylcyclohexylamine was dissolved in 20ml of methylene chloride, 810. Mu.l (0.013 mol,97%,1.3 eq) of methyl iodide was added dropwise with magnetic stirring at room temperature, the mixture was refluxed for 1 to 2 hours after the addition was completed, filtered after the completion of the reaction, dried to obtain a pale yellow solid, and 1.14g of a pale yellow solid of N, N, N-trimethylcyclohexylammonium salt product was obtained by recrystallization, GC:97%, separation recovery rate: 81%.
Example 3:
the present example is a process for the preparation of an iodo-N, N, N-trimethylcyclohexylammonium salt with dichloromethane as the reaction solvent, according to the following reaction scheme:
wherein: the molar ratio of N, N-dimethylcyclohexylamine to methyl iodide is 1:1.5.
The specific experimental process is as follows:
in a 50ml three-necked flask, 1.28g (0.01 mol,97%,1 eq) of N, N-dimethylcyclohexylamine was dissolved in 20ml of methylene chloride, 935. Mu.l (0.015 mol,97%,1.5 eq) of methyl iodide was added dropwise with magnetic stirring at room temperature, the mixture was refluxed for 1 to 2 hours after the addition was completed, and after the completion of the reaction, the mixture was filtered and dried to obtain a pale yellow solid, and 1.27g of a pale yellow solid of N, N, N-trimethylcyclohexylammonium salt product was obtained by recrystallization, GC:96%, separation recovery: 90%.
Example 4:
the implementation is a preparation method of iodinated N, N, N-trimethyl cyclohexylammonium salt by using methylene dichloride as a reaction solvent, and the preparation method comprises the following reaction formula:
wherein: the molar ratio of N, N-dimethylcyclohexylamine to methyl iodide is 1:1.5.
The specific experimental process is as follows:
in a 50ml three-necked flask, 1.30g (0.01 mol,97%,1 eq) of N, N-dimethylcyclohexylamine was dissolved in 20ml of acetone, 935. Mu.l (0.015 mol,97%,1.5 eq) of methyl iodide was added dropwise with magnetic stirring at room temperature, the mixture was refluxed for 1 to 2 hours after the addition was completed, filtered after the completion of the reaction, dried to obtain a pale yellow solid, and 1.20g of a pale yellow solid of N, N, N-trimethylcyclohexylammonium salt product was obtained by recrystallization, GC:96%, separation recovery: 85%.
While embodiments of the invention have been illustrated and described, it will be apparent that the embodiments described are merely some, but not all embodiments of the invention. Based on the embodiments of the present invention, it will be understood by those skilled in the art that all other embodiments which may be obtained from numerous changes, modifications, substitutions and alterations of these embodiments without departing from the spirit and principles of the present invention are within the scope of the present invention.
Claims (4)
1. A preparation method of iodo N, N, N-trimethyl cyclohexylammonium salt is characterized by comprising the following steps: n, N-dimethyl cyclohexylamine is taken as a raw material to be added into a solvent, methyl iodide is added dropwise under the condition of room temperature, and then N, N, N-trimethyl cyclohexylammonium salt is synthesized by a one-pot method.
2. The method for preparing the iodo N, N, N-trimethyl cyclohexylammonium salt according to claim 1, wherein the method comprises the following steps: the molar ratio of the N, N-dimethylcyclohexylamine to methyl iodide is 1:1.0 to 1.5.
3. The method for preparing the iodo N, N, N-trimethyl cyclohexylammonium salt according to claim 1, wherein the method comprises the following steps: the reaction is carried out, wherein the dissolution is one of dichloromethane and acetone.
4. The method for preparing the iodo N, N, N-trimethyl cyclohexylammonium salt according to claim 1, wherein the method comprises the following steps: and dropwise adding methyl iodide, reacting and stirring for 1-2 h, filtering and drying after TLC detection reaction is finished, and finally obtaining the iodo N, N, N-trimethyl cyclohexylammonium salt.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310609293.2A CN116693399A (en) | 2023-05-29 | 2023-05-29 | Preparation method of iodo-N, N, N-trimethyl-cyclohexenyl ammonium salt |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310609293.2A CN116693399A (en) | 2023-05-29 | 2023-05-29 | Preparation method of iodo-N, N, N-trimethyl-cyclohexenyl ammonium salt |
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| Publication Number | Publication Date |
|---|---|
| CN116693399A true CN116693399A (en) | 2023-09-05 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310609293.2A Pending CN116693399A (en) | 2023-05-29 | 2023-05-29 | Preparation method of iodo-N, N, N-trimethyl-cyclohexenyl ammonium salt |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN116693399A (en) |
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2023
- 2023-05-29 CN CN202310609293.2A patent/CN116693399A/en active Pending
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