CN116947675A - Preparation method of organic intermediate N- (1-methylcyclopentyl) -benzamide - Google Patents
Preparation method of organic intermediate N- (1-methylcyclopentyl) -benzamide Download PDFInfo
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- CN116947675A CN116947675A CN202310948675.8A CN202310948675A CN116947675A CN 116947675 A CN116947675 A CN 116947675A CN 202310948675 A CN202310948675 A CN 202310948675A CN 116947675 A CN116947675 A CN 116947675A
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- CN
- China
- Prior art keywords
- methylcyclopentyl
- benzamide
- sulfuric acid
- methylcyclopentanol
- benzonitrile
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- UHXZKPJGQWZDTL-UHFFFAOYSA-N n-(1-methylcyclopentyl)benzamide Chemical compound C=1C=CC=CC=1C(=O)NC1(C)CCCC1 UHXZKPJGQWZDTL-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title abstract description 10
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims abstract description 57
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 44
- 238000006243 chemical reaction Methods 0.000 claims abstract description 20
- CAKWRXVKWGUISE-UHFFFAOYSA-N 1-methylcyclopentan-1-ol Chemical compound CC1(O)CCCC1 CAKWRXVKWGUISE-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000002904 solvent Substances 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 12
- 230000035484 reaction time Effects 0.000 claims abstract description 10
- 239000007787 solid Substances 0.000 claims abstract description 10
- 238000001035 drying Methods 0.000 claims abstract description 9
- 238000001914 filtration Methods 0.000 claims abstract description 9
- 239000005457 ice water Substances 0.000 claims abstract description 9
- 238000002386 leaching Methods 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000006482 condensation reaction Methods 0.000 claims abstract description 8
- 239000002994 raw material Substances 0.000 claims abstract description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 30
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 6
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 3
- 235000019260 propionic acid Nutrition 0.000 claims description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 3
- 238000005265 energy consumption Methods 0.000 abstract description 3
- 238000009776 industrial production Methods 0.000 abstract description 3
- 238000000746 purification Methods 0.000 abstract description 3
- 238000000926 separation method Methods 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 230000001376 precipitating effect Effects 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- XNSBZWPLJHUBPA-UHFFFAOYSA-N n,1-dimethylcyclopentan-1-amine Chemical compound CNC1(C)CCCC1 XNSBZWPLJHUBPA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/06—Preparation of carboxylic acid amides from nitriles by transformation of cyano groups into carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
- C07C231/24—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method of an organic intermediate N- (1-methylcyclopentyl) -benzamide, and relates to the technical field of organic synthesis. The method comprises the following steps: s1: 1-methylcyclopentanol, benzonitrile and sulfuric acid are used as raw materials, sulfuric acid is dropwise added in ice bath for condensation reaction in the presence of a solvent to prepare N- (1-methylcyclopentyl) -benzamide; s2: after the reaction is finished, slowly pouring the reaction solution into ice water, precipitating a large amount of off-white solid, filtering, leaching with water, and drying to obtain an organic intermediate N- (1-methylcyclopentyl) -benzamide; in the step S1, the dosage proportion of the 1-methylcyclopentanol, the benzonitrile, the sulfuric acid and the solvent is as follows by mass: 1-methylcyclopentanol, benzonitrile, sulfuric acid, solvent=1:1.08-1.34:1.03-1.27:4.25-5.61. The invention has the advantages of simple separation and purification process, short reaction time, high product yield up to more than 94%, low energy consumption and low cost, and is an ideal process for realizing industrial production.
Description
Technical Field
The invention relates to the technical field of organic synthesis, in particular to a preparation method of an organic intermediate N- (1-methylcyclopentyl) -benzamide.
Background
The organic intermediate N- (1-methylcyclopentyl) -benzamide is an important fine substanceThe intermediate can be used for synthesizing a medical intermediate N-methyl-1-methylcyclopentylamine. Because the molecule contains amide groups, the chemical property is relatively active, and a series of chemical reactions such as alkylation, addition and the like can occur. The molecular formula of the target product is C 13 H 17 NO, molecular weight: 203.28.
the appearance of the N- (1-methylcyclopentyl) -benzamide is off-white solid powder, and few reports are made in the domestic literature on the synthesis of the N- (1-methylcyclopentyl) -benzamide, so that the research on the preparation method of the N- (1-methylcyclopentyl) -benzamide has very important industrial application value.
Disclosure of Invention
The invention aims to provide a preparation method of an organic intermediate N- (1-methylcyclopentyl) -benzamide, which aims to solve the problems in the background art.
In order to achieve the above purpose, the present invention provides the following technical solutions: a preparation method of an organic intermediate N- (1-methylcyclopentyl) -benzamide comprises the following steps:
s1: 1-methylcyclopentanol, benzonitrile and sulfuric acid are used as raw materials, sulfuric acid is dropwise added in ice bath for condensation reaction in the presence of a solvent to prepare N- (1-methylcyclopentyl) -benzamide;
s2: after the reaction is finished, the reaction solution is slowly poured into ice water to precipitate a large amount of off-white solid, and the organic intermediate N- (1-methylcyclopentyl) -benzamide can be obtained through filtering, water leaching and drying.
Further, in the step S1, the ratio of the amounts of the 1-methylcyclopentanol, the benzonitrile, the sulfuric acid and the solvent is as follows by mass: 1-methylcyclopentanol, benzonitrile, sulfuric acid, solvent=1:1.08-1.34:1.03-1.27:4.25-5.61.
Further, in the step S1, the solvent is acetic acid or propionic acid, preferably acetic acid.
Further, in the step S1, the condensation reaction temperature is 25-35 ℃ and the condensation reaction time is 15-24h.
Compared with the prior art, the invention has the beneficial effects that:
the preparation method of the organic intermediate N- (1-methylcyclopentyl) -benzamide is different from the prior art in that the separation and purification process is simple, the reaction time is short, the product yield is high and reaches more than 94%, the energy consumption is low, and the cost is low, so that the preparation method is an ideal process for realizing industrial production.
Drawings
FIG. 1 is a molecular structure diagram of N- (1-methylcyclopentyl) -benzamide according to the present invention.
Detailed Description
The following description of the embodiments of the present invention will be made clearly and completely with reference to the accompanying drawings, in which it is apparent that the embodiments described are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
As shown in fig. 1, the present invention provides a technical solution: a preparation method of an organic intermediate N- (1-methylcyclopentyl) -benzamide.
The method adopts 1-methylcyclopentanol, benzonitrile and sulfuric acid as raw materials, the 1-methylcyclopentanol and the benzonitrile are dropwise added with sulfuric acid in the presence of a solvent for condensation reaction in an ice bath, after the reaction is finished, the reaction solution is slowly poured into ice water, a large amount of off-white solid is separated out, and the organic intermediate N- (1-methylcyclopentyl) -benzamide can be obtained after filtering, leaching with water and drying. The solvent is acetic acid or propionic acid, preferably acetic acid; the reaction temperature is 25-35 ℃, the reaction time is 15-24 hours, wherein the dosage proportion of 1-methylcyclopentanol, benzonitrile and sulfuric acid is as follows by mass: 1-methylcyclopentanol, benzonitrile, sulfuric acid, solvent=1:1.08-1.34:1.03-1.27:4.25-5.61.
Example 1:
in a 500mL four-necked flask equipped with a thermometer, 127.5g of acetic acid, 30g of 1-methylcyclopentanol and 32.4g of benzonitrile were added, the stirrer was started, 31.5g of sulfuric acid was added dropwise under an ice bath, and the reaction time at room temperature was 15-24 hours after the dropwise addition. After the reaction is finished, the reaction solution is slowly poured into 1.0L of ice water to precipitate a large amount of off-white solid, and the organic intermediate N- (1-methylcyclopentyl) -benzamide product with the product yield of 94.28% can be obtained through filtering, leaching with water and drying.
Example 2:
in a 500mL four-necked flask equipped with a thermometer, 127.5g of acetic acid, 30g of 1-methylcyclopentanol and 36.0g of benzonitrile are added, a condenser is arranged, a stirrer is started, 31.5g of sulfuric acid is added dropwise under an ice bath, and the reaction time is 15-24 hours at room temperature after the dropwise addition. After the reaction is finished, the reaction solution is slowly poured into 1.0L of ice water to precipitate a large amount of off-white solid, and the organic intermediate N- (1-methylcyclopentyl) -benzamide product with the product yield of 95.41% can be obtained through filtering, leaching with water and drying.
Example 3:
in a 500mL four-necked flask equipped with a thermometer, 127.5g of acetic acid, 30g of 1-methylcyclopentanol and 36.0g of benzonitrile are added, a condenser is arranged, a stirrer is started, 39.0g of sulfuric acid is added dropwise under an ice bath, and the reaction time is 15-24 hours at room temperature after the dropwise addition. After the reaction is finished, the reaction solution is slowly poured into 1.0L of ice water to precipitate a large amount of off-white solid, and the organic intermediate N- (1-methylcyclopentyl) -benzamide product with the product yield of 95.93% can be obtained through filtering, leaching with water and drying.
Example 4:
in a 500mL four-necked flask equipped with a thermometer, 255g of acetic acid, 30g of 1-methylcyclopentanol and 36.0g of benzonitrile were added, a condenser was equipped, a stirrer was started, 31.5g of sulfuric acid was added dropwise under an ice bath, and the reaction time at room temperature was 15-24 hours after the dropwise addition. After the reaction is finished, the reaction solution is slowly poured into 1.0L of ice water to precipitate a large amount of off-white solid, and the organic intermediate N- (1-methylcyclopentyl) -benzamide product with the product yield of 94.26% can be obtained through filtering, leaching with water and drying.
Example 5:
in a 500mL four-necked flask equipped with a thermometer, 127.5g of acetic acid, 30g of 1-methylcyclopentanol and 39.0g of benzonitrile were added, a condenser was equipped, a stirrer was started, 39.0g of sulfuric acid was added dropwise under an ice bath, and the reaction time at room temperature was 15-24 hours after the dropwise addition. After the reaction is finished, the reaction solution is slowly poured into 1.0L of ice water to precipitate a large amount of off-white solid, and the organic intermediate N- (1-methylcyclopentyl) -benzamide product with the product yield of 96.02% can be obtained through filtering, leaching with water and drying.
The invention synthesizes the organic intermediate N- (1-methylcyclopentyl) -benzamide by using 1-methylcyclopentanol, benzonitrile and sulfuric acid as raw materials, has simple separation and purification process, high product yield which reaches more than 94%, low energy consumption and low cost, and is an ideal process for realizing industrial production.
Although embodiments of the present invention have been shown and described, it will be understood by those skilled in the art that various changes, modifications, substitutions and alterations can be made hereto without departing from the spirit and scope of the invention as defined by the appended embodiments and equivalents thereof.
Claims (4)
1. A method for preparing an organic intermediate N- (1-methylcyclopentyl) -benzamide, which is characterized by comprising the following steps:
s1: 1-methylcyclopentanol, benzonitrile and sulfuric acid are used as raw materials, sulfuric acid is dropwise added in ice bath for condensation reaction in the presence of a solvent to prepare N- (1-methylcyclopentyl) -benzamide;
s2: after the reaction is finished, the reaction solution is slowly poured into ice water to precipitate a large amount of off-white solid, and the organic intermediate N- (1-methylcyclopentyl) -benzamide can be obtained through filtering, water leaching and drying.
2. The method for preparing the organic intermediate N- (1-methylcyclopentyl) -benzamide according to claim 1, wherein the method comprises the following steps: in the step S1, the dosage proportion of the 1-methylcyclopentanol, the benzonitrile, the sulfuric acid and the solvent is as follows by mass: 1-methylcyclopentanol, benzonitrile, sulfuric acid, solvent=1:1.08-1.34:1.03-1.27:4.25-5.61.
3. The method for preparing the organic intermediate N- (1-methylcyclopentyl) -benzamide according to claim 1, wherein the method comprises the following steps: in the step S1, the solvent is acetic acid or propionic acid, preferably acetic acid.
4. The method for preparing the organic intermediate N- (1-methylcyclopentyl) -benzamide according to claim 1, wherein the method comprises the following steps: in the step S1, the condensation reaction temperature is 25-35 ℃, and the condensation reaction time is 15-24h.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310948675.8A CN116947675A (en) | 2023-07-31 | 2023-07-31 | Preparation method of organic intermediate N- (1-methylcyclopentyl) -benzamide |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310948675.8A CN116947675A (en) | 2023-07-31 | 2023-07-31 | Preparation method of organic intermediate N- (1-methylcyclopentyl) -benzamide |
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| Publication Number | Publication Date |
|---|---|
| CN116947675A true CN116947675A (en) | 2023-10-27 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310948675.8A Pending CN116947675A (en) | 2023-07-31 | 2023-07-31 | Preparation method of organic intermediate N- (1-methylcyclopentyl) -benzamide |
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| Country | Link |
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| CN (1) | CN116947675A (en) |
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2023
- 2023-07-31 CN CN202310948675.8A patent/CN116947675A/en active Pending
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