CN101503386B - Method for refining 1-amyl-3-(4-methyl-1-naphthoyl) indole - Google Patents
Method for refining 1-amyl-3-(4-methyl-1-naphthoyl) indole Download PDFInfo
- Publication number
- CN101503386B CN101503386B CN2009100299099A CN200910029909A CN101503386B CN 101503386 B CN101503386 B CN 101503386B CN 2009100299099 A CN2009100299099 A CN 2009100299099A CN 200910029909 A CN200910029909 A CN 200910029909A CN 101503386 B CN101503386 B CN 101503386B
- Authority
- CN
- China
- Prior art keywords
- indoles
- isophthalic acid
- methyl isophthalic
- amyl group
- naphthoyl base
- 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.)
- Expired - Fee Related
Links
Landscapes
- Indole Compounds (AREA)
Abstract
The invention discloses a method for refining 1-pentyl-3-(4-methyl-1-naphthacyl) indole, relating to a method for refining and purifying the 1-pentyl-3-(4-methyl-1-naphthacyl) indole. The refining method is as below: an oily matter crude of the 1-pentyl-3-(4-methyl-1-naphthacyl) indole, which is obtained through preparation, is added with 75-95 percent of ethanol aqueous solution; the weight ratio of the an oily matter crude of the 1-pentyl-3-(4-methyl-1-naphthacyl) indole and the an oily matter crude of the 1-pentyl-3-(4-methyl-1-naphthacyl) indole is 1 : 1-20; the mixture is subject to violent stirring for 0.5-4 h at a temperature of 5-30 DEG C; filtration and then vacuum drying are carried out, wherein the vacuity is 120-200 Pa, the drying temperature is 2-40 DEG C, and the drying time is 4-10 h; and then, the finished product of the 1-pentyl-3-(4-methyl-1-naphthacyl) indole is obtained.
Description
Technical field
What the method for a kind of refining 1-amyl group-3-of the present invention (4-methyl isophthalic acid-naphthoyl base) indoles related to is the process for refining and purifying of a kind of 1-amyl group-3-(4-methyl isophthalic acid-naphthoyl base) indoles.
Background technology
1-amyl group-3-(4-methyl isophthalic acid-naphthoyl base) indoles, English 1-Pentyl-3-(4-methyl-1-naphthoyl) indole by name
Structural formula
Bang (Cannabis sativa L.) and derivative thereof are used for medicine and existing hundreds of years of entertainment purposes.The main active ingredient of hemp and hashish has been defined as Δ
9-tetrahydrocannabinol (Δ
9-THC).The detailed Δ that studies show that
9-THC and other member's of cannaboid family biological action is to be called as acceptor CB1 and CB2 and the G-albumen coupling by two kinds to take place.The CB1 acceptor mainly is present in maincenter and the peripheral nervous system, but also exists a small amount of in some peripheral organs.The CB2 acceptor mainly is present in Lymphoid tissue and the cell.Identified the Cannabined receptor endogenic ligand of three kinds of derivatives, they all are agonist, activity and Δ
9-THC is similar, is used for that calmness, cooling, intestines are fixed, anti-nociception, pain relieving, catalepsy, antiemetic and stimulate appetite etc.
1-amyl group-3-(4-methyl isophthalic acid-naphthoyl base) indoles is the conditioning agent of Cannabined receptor, thereby can be used for treatment, prevention and inhibition by Cannabined receptor adjusting diseases associated.The method for preparing 1-amyl group-3-(4-methyl isophthalic acid-naphthoyl base) indoles is expressed as follows with chemical equation:
Consult relevant documents and materials, have only method by column chromatography for the purifying of 1-amyl group-3-(4-methyl isophthalic acid-naphthoyl base) indoles, this purification process not only yield is low, and the cost height, is difficult to realize suitability for industrialized production.
Summary of the invention
The objective of the invention is provides a kind of refining 1-amyl group-3-(4-methyl isophthalic acid-naphthoyl base) method of indoles at above-mentioned weak point, is a kind of raising yield, reduces cost, and realizes the method for suitability for industrialized production.The method that the present invention makes with extra care 1-amyl group-3-(4-methyl isophthalic acid-naphthoyl base) indoles adopts 1-amyl group-3-(4-methyl isophthalic acid-naphthoyl base), and indoles solubleness in 75%～95% aqueous ethanolic solution is low, and the impurity that is contained in the crude product is soluble in the character of 75%～95% aqueous ethanolic solution and reach the purified purpose; The highly finished product proterties of gained is stable simultaneously; Treating process is more conducive to industrialization, and yield also improves greatly.
The method of a kind of refining 1-amyl group-3-(4-methyl isophthalic acid-naphthoyl base) indoles realizes by following scheme:
The method of a kind of refining 1-amyl group-3-(4-methyl isophthalic acid-naphthoyl base) indoles; it is characterized in that in process prepares the oily matter crude product of 1-amyl group-3-(4-methyl isophthalic acid-naphthoyl base) indoles, adding 75%～95% aqueous ethanolic solution; 1-amyl group-3-(4-methyl isophthalic acid-naphthoyl base) the crude product weight of indoles and the weight ratio of aqueous ethanolic solution are 1: 1～20; vigorous stirring is 0.5～4 hour in 5～30 ℃ environment; filter; vacuum-drying; vacuum tightness is 120～200Pa; drying temperature is 20～40 ℃; be 4～10 hours time of drying, gets 1-amyl group-3-(4-methyl isophthalic acid-naphthoyl base) indoles highly finished product.
Describedly in the oily matter crude product that process prepares, add aqueous ethanolic solution, aqueous ethanolic solution concentration preferred 85%～95%.
Describedly in the oily matter crude product that process prepares, add aqueous ethanolic solution, it is characterized in that described 1-amyl group-3-(4-methyl isophthalic acid-naphthoyl base) the oily matter crude product of indoles and the weight proportion of aqueous ethanolic solution are 1: 5～10.
The method of described refining 1-amyl group-3-(4-methyl isophthalic acid-naphthoyl base) indoles is characterized in that after adding aqueous ethanolic solution vigorous stirring in 10～20 ℃ environment.
The method of a kind of refining 1-amyl group-3-(4-methyl isophthalic acid-naphthoyl base) indoles, adopt 1-amyl group-3-(4-methyl isophthalic acid-naphthoyl base) indoles solubleness in 75%～95% aqueous ethanolic solution low, and the impurity that is contained in the oily matter crude product of 1-amyl group-3-(4-methyl isophthalic acid-naphthoyl base) indoles is soluble in the character of 75%～95% aqueous ethanolic solution and reaches the purified purpose, and the highly finished product proterties of gained is stable simultaneously; Treating process is more conducive to industrialization, and yield also improves greatly.Higher through the inventive method purified 1-amyl group-3-(4-methyl isophthalic acid-naphthoyl base) indoles yield and content, and method easy, be easier to industrialization, avoided the process of column chromatography purification used in the existing reported in literature.
After the present invention purifies, adopt nucleus magnetic resonance, mass spectrum, its structure of infrared analysis to be 1-amyl group-3-(4-methyl isophthalic acid-naphthoyl base) indoles; Adopt high efficiency liquid phase chromatographic analysis method, 1-amyl group-3-(4-methyl isophthalic acid-naphthoyl base) indoles content is greater than 98%; Refining yield is higher than 50%.
Embodiment
Further specify the present invention below by example.Should understand accurately that process for purification in the example of the present invention is only used for the present invention is described and the restriction that provides, so, under method prerequisite of the present invention, simple modifications of the present invention is all belonged to protection scope of the present invention.
Example 1:
Add 75% aqueous ethanolic solution 100g in the oily matter crude product of 10g 1-amyl group-3-(4-methyl isophthalic acid-naphthoyl base) indoles; vigorous stirring is 0.5 hour in 5 ℃ environment; filter; vacuum-drying; vacuum tightness is 200Pa, and the vacuum-drying temperature is 20 ℃, and be 4 hours time of drying; get 1-amyl group-3-(4-methyl isophthalic acid-naphthoyl base) indoles highly finished product 4.2g, yield: 50%.Efficient liquid phase chromatographic analysis, content is greater than 98.5%.
Example 2:
Add 85% aqueous ethanolic solution 50g in the oily matter crude product of 10g 1-amyl group-3-(4-methyl isophthalic acid-naphthoyl base) indoles; vigorous stirring is 0.5 hour in 10 ℃ environment; filter; vacuum-drying; vacuum tightness is 180Pa, and the vacuum-drying temperature is 20 ℃, and be 4 hours time of drying; get 1-amyl group-3-(4-methyl isophthalic acid-naphthoyl base) indoles highly finished product 5.1g, yield: 51%.Efficient liquid phase chromatographic analysis, content is greater than 98.5%.
Example 3:
Add 95% aqueous ethanolic solution 50g in the oily matter crude product of 10g 1-amyl group-3-(4-methyl isophthalic acid-naphthoyl base) indoles; vigorous stirring is 2 hours in 20 ℃ environment; filter; vacuum-drying; vacuum tightness is 160 Pa, and the vacuum-drying temperature is 20 ℃, and be 4 hours time of drying; get 1-amyl group-3-(4-methyl isophthalic acid-naphthoyl base) indoles highly finished product 5.9g, yield: 59%.Efficient liquid phase chromatographic analysis, content is greater than 98.5%.
Example 4:
Add 95% aqueous ethanolic solution 50g in the oily matter crude product of 10g 1-amyl group-3-(4-methyl isophthalic acid-naphthoyl base) indoles; vigorous stirring is 2 hours in 15 ℃ environment; filter; vacuum-drying; vacuum tightness is 150Pa, and the vacuum-drying temperature is 20 ℃, and be 5 hours time of drying; get 1-amyl group-3-(4-methyl isophthalic acid-naphthoyl base) indoles highly finished product 5.6g, yield: 56%.Efficient liquid phase chromatographic analysis, content is greater than 98.5%.
Example 5:
Add 95% aqueous ethanolic solution 150g in the oily matter crude product of 10g 1-amyl group-3-(4-methyl isophthalic acid-naphthoyl base) indoles; vigorous stirring is 4 hours in 30 ℃ environment; filter; vacuum-drying; vacuum tightness is 120Pa, and the vacuum-drying temperature is 30 ℃, and be 7 hours time of drying; get 1-amyl group-3-(4-methyl isophthalic acid-naphthoyl base) indoles highly finished product 6.4g, yield: 64%.Efficient liquid phase chromatographic analysis, content is greater than 98.5%.
Example 6:
Add 95% aqueous ethanolic solution 100g in the oily matter crude product of 10g 1-amyl group-3-(4-methyl isophthalic acid-naphthoyl base) indoles; vigorous stirring is 4 hours in 10 ℃ environment; filter; vacuum-drying; vacuum tightness is 120Pa, and the vacuum-drying temperature is 30 ℃, and be 10 hours time of drying; get 1-amyl group-3-(4-methyl isophthalic acid-naphthoyl base) indoles highly finished product 7.2g, yield: 72%.Efficient liquid phase chromatographic analysis, content is greater than 98.5%.
Example 7:
Add 95% aqueous ethanolic solution 200g in the oily matter crude product of 10g 1-amyl group-3-(4-methyl isophthalic acid-naphthoyl base) indoles; vigorous stirring is 4 hours in 20 ℃ environment; filter; vacuum-drying; vacuum tightness is 120Pa, and the vacuum-drying temperature is 40 ℃, and be 5 hours time of drying; get 1-amyl group-3-(4-methyl isophthalic acid-naphthoyl base) indoles highly finished product 7.7g, yield: 77%.Efficient liquid phase chromatographic analysis, content is greater than 98.5%.
Claims (4)
1. the method for a refining 1-amyl group-3-(4-methyl isophthalic acid-naphthoyl base) indoles; it is characterized in that in process prepares the oily matter crude product of 1-amyl group-3-(4-methyl isophthalic acid-naphthoyl base) indoles, adding 75%～95% aqueous ethanolic solution; 1-amyl group-3-(4-methyl isophthalic acid-naphthoyl base) the oily matter crude product of indoles and the weight proportion of aqueous ethanolic solution are 1: 1～20; vigorous stirring is 0.5～4 hour in 5～30 ℃ environment; filter; vacuum-drying; vacuum tightness is 120～200Pa; drying temperature is 20～40 ℃; be 4～10 hours time of drying, gets the highly finished product of 1-amyl group-3-(4-methyl isophthalic acid-naphthoyl base) indoles.
2. the method for a kind of refining 1-amyl group-3-according to claim 1 (4-methyl isophthalic acid-naphthoyl base) indoles; it is characterized in that adding aqueous ethanolic solution in process prepares the oily matter crude product of 1-amyl group-3-(4-methyl isophthalic acid-naphthoyl base) indoles, aqueous ethanolic solution concentration selects 85%～95% for use.
3. the method for a kind of refining 1-amyl group-3-according to claim 1 (4-methyl isophthalic acid-naphthoyl base) indoles is characterized in that described 1-amyl group-3-(4-methyl isophthalic acid-naphthoyl base) the oily matter crude product of indoles and the weight proportion of aqueous ethanolic solution are 1: 5～10.
4. the method for a kind of refining 1-amyl group-3-according to claim 1 (4-methyl isophthalic acid-naphthoyl base) indoles, its feature after adding aqueous ethanolic solution in 10～20 ℃ environment vigorous stirring.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009100299099A CN101503386B (en) | 2009-03-27 | 2009-03-27 | Method for refining 1-amyl-3-(4-methyl-1-naphthoyl) indole |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009100299099A CN101503386B (en) | 2009-03-27 | 2009-03-27 | Method for refining 1-amyl-3-(4-methyl-1-naphthoyl) indole |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101503386A CN101503386A (en) | 2009-08-12 |
| CN101503386B true CN101503386B (en) | 2011-06-08 |
Family
ID=40975779
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2009100299099A Expired - Fee Related CN101503386B (en) | 2009-03-27 | 2009-03-27 | Method for refining 1-amyl-3-(4-methyl-1-naphthoyl) indole |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101503386B (en) |
-
2009
- 2009-03-27 CN CN2009100299099A patent/CN101503386B/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN101503386A (en) | 2009-08-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN112638873B (en) | Refining method of indocyanine green | |
| CN101942001A (en) | Purification method of loteprednol etabonate | |
| CN108947949B (en) | Anxiolytic deuterated compounds and medical application thereof | |
| CN110818585B (en) | Separation method for simultaneously preparing five dopamine compounds from aspongopus | |
| CN101774875A (en) | Method for synthesizing piperlongumine compounds | |
| CN100357358C (en) | Method for preparing licopin | |
| CN102911235A (en) | Method for producing ursodesoxycholic acid by using chenodeoxycholic acid as raw material | |
| CN102775387A (en) | Method for refining fasudil hydrochloride | |
| CN101503386B (en) | Method for refining 1-amyl-3-(4-methyl-1-naphthoyl) indole | |
| CA3066772A1 (en) | Process for the preparation of standardized composition of arjunoglucoside from the bark of terminalia arjuna | |
| CN101613278B (en) | Industrial technology for quickly extracting high-purity chlorogenic acid from sweet potato leaf | |
| CN107973835B (en) | Natural mixed phytosterol catechin, preparation method and application | |
| CN101817827A (en) | Method for preparing sesamin from sesame | |
| CN102134247B (en) | Xanthotoxol derivative and new composite method thereof | |
| CN107033114B (en) | Method for separating and purifying dihydromyricetin | |
| CN101928277A (en) | Preparation method of 4-methyl-3-[[4-(3-pyridyl)-2-pyrimidyl]amino]benzoic acid, related intermediate and application thereof | |
| CN104447902A (en) | High yield and easy purification preparation method of gastrodin derivative | |
| CN102532111A (en) | Method for extracting puerarin from traditional Chinese medicine kudzu | |
| CN105669672B (en) | A kind of pyrido-pyrimidines and preparation method thereof | |
| CN104193753A (en) | Method for preparing photosensitizer HPPH from taxus chinensis branch and leaf extracts | |
| CN103193712B (en) | A kind of preparation method of N-BETA-Alanyl-L-histidine | |
| CN106883185B (en) | Preparation method of 4-chloro-2-trifluoromethylpyrimidine | |
| CN109651391A (en) | A method of qinghaosu is recycled from qinghaosu recrystallization waste material | |
| CN102675105A (en) | Phenolic compound in tobacco as well as preparation method and application thereof | |
| JP4136355B2 (en) | Method for producing camptothecin |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C17 | Cessation of patent right | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20110608 Termination date: 20120327 |