CN102276576A - benzamide compound and preparation method thereof - Google Patents
benzamide compound and preparation method thereof Download PDFInfo
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- CN102276576A CN102276576A CN201110148165XA CN201110148165A CN102276576A CN 102276576 A CN102276576 A CN 102276576A CN 201110148165X A CN201110148165X A CN 201110148165XA CN 201110148165 A CN201110148165 A CN 201110148165A CN 102276576 A CN102276576 A CN 102276576A
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Abstract
The invention discloses a benzamide compound and a preparation method thereof, aiming at solving the technical problems that in the existing preparation method of benzamide, because toxic substances such as potassium cyanide and sodium hydride, environmental pollution is easily caused. The technical scheme comprises the following steps: carrying out a reaction on benzoic acid containing a substituent group and succinimide trifluoroacetate at room temperature so as to generate succinimide ester of substituted benzoic acid; and then carrying out a reaction on succinimide ester of substituted benzoic acid and piperidine or morphine or pyrrolidine or pyrazine at room temperature so as to prepare the benzamide compound. In the invention, because potassium cyanide and sodium hydride are not used, the pollution of a preparation process on environment is relieved; reactions are carried out at room temperature, reaction conditions are extremely mild, reaction yield is high, reaction is generally finished within 5 hours, and reaction elapsed time is short; the posttreatment method of the reaction product is simple, and the product is easy to purify and separate; and the product is washed by just using diluted hydrochloric acid, is dried by just using a drying agent and is purified by using a recrystallization mode.
Description
Technical field
The present invention relates to a kind of compound, particularly a kind of benzamide compounds; The preparation method who also relates to this benzamide compounds.
Background technology
Document 1 " Journal of Organic Chemistry, 44 (25): 4597-603; 1979 " a kind of preparation method of benzamide compounds is disclosed; this method adopts piperonylaldehyde, morphine quinoline under potassium cyanide and p-methyl benzenesulfonic acid effect; with water is solvent; obtain intermediate product; more successively with metachloroperbenzoic acid and sodium hydride effect; generate benzamide compounds through polystep reaction, route is as follows:
Though this method has been prepared benzamide compounds, the preparation process complexity, and adopt highly toxic substances such as potassium cyanide, sodium hydride in the preparation, cause environmental pollution easily.
Summary of the invention
For the preparation method that overcomes existing benzamide compounds owing to adopt highly toxic substance potassium cyanide, sodium hydride and cause the deficiency of environmental pollution easily, the invention provides a kind of benzamide compounds and preparation method thereof, this method is at first utilized the succinimide ester that contains reaction generation substituted benzoic acid under substituent phenylformic acid and the trifluoroacetic acid succinimide ester room temperature, secondly, the succinimide ester of substituted benzoic acid and hexahydropyridine or morphine quinoline or tetramethyleneimine prepared in reaction obtain benzamide compounds under the room temperature, owing to do not use potassium cyanide, sodium hydride can alleviate the pollution of preparation process to environment.
The technical solution adopted for the present invention to solve the technical problems is: a kind of benzamide compounds, its structural formula is
A kind of benzamide compounds, its structural formula is
A kind of preparation method of above-mentioned benzamide compounds is characterized in adopting following steps:
(a) be 1: 15～1: 20 batching according to containing the mass/volume ratio of substituting group phenylformic acid with methylene dichloride, to contain the substituting group phenylformic acid is dissolved in the methylene dichloride, stirring and dissolving, according to containing the mass/volume ratio of substituting group phenylformic acid with triethylamine or pyridine is to add catalyst of triethylamine or pyridine in 2: 1～2: 1.5, obtains reaction mixture.
(b) in the reaction mixture of step (a) preparation,, add the trifluoroacetic acid succinimide ester according to containing substituting group phenylformic acid and trifluoroacetic acid succinimide ester mol ratio 1: 1～1: 3.Stirring reaction is 2～5 hours under the room temperature.Reaction process tracks to thin-layer chromatography and reacts completely, and after reaction finishes, the hydrochloric acid soln of reaction mixture with 1mol/L is washed three times, and anhydrous sodium sulfate drying steams solvent, obtains the reaction intermediate of white solid.
(c) intermediate product that step (b) is prepared is dissolved in trichloromethane or the dichloromethane solvent, the consumption of trichloromethane or methylene dichloride is 1: 12～1: 15 batching according to the mass/volume ratio of intermediate product and trichloromethane or methylene dichloride, after stirring, according to 8～11% of reaction soln cumulative volume, add the morphine quinoline, perhaps hexahydropyridine, perhaps tetramethyleneimine, perhaps pyrazine, stirring reaction is 2～5 hours under the room temperature, reaction process is followed the tracks of with thin-layer chromatography, after reaction finishes, hydrochloric acid soln with 1mol/L washs three times, and anhydrous sodium sulfate drying steams solvent, separate and purify, obtain benzamide compounds.
The invention has the beneficial effects as follows: owing to utilize the succinimide ester that contains reaction generation substituted benzoic acid under substituent phenylformic acid and the trifluoroacetic acid succinimide ester room temperature, secondly, the succinimide ester of substituted benzoic acid and hexahydropyridine or morphine quinoline or tetramethyleneimine or pyrazine prepared in reaction obtain benzamide compounds under the room temperature, owing to do not use potassium cyanide, sodium hydride, can alleviate the pollution of preparation process to environment.Reaction is all at room temperature carried out, reaction conditions as mild as a dove, the reaction yield height, reaction generally can be finished in 5 hours, reaction time consumption is short.The post-treating method of reaction product is simple, and the product separation of purifying easily only needs get final product refined product with dilute hydrochloric acid washing, siccative drying, means re-crystallization.
Below in conjunction with embodiment the present invention is elaborated.
Embodiment
Embodiment 1: the 10g piperinic acid is dissolved in the 150ml methylene dichloride, add the 5ml triethylamine, stirring and dissolving adds 20g trifluoroacetic acid succinimide ester, stirring at room, thin-layer chromatography (TLC) tracks to and reacts completely, and 2 hours reaction times is after reaction finishes, dilute hydrochloric acid with 1mol/L washs three times, use anhydrous sodium sulfate drying, steam solvent, obtain white powder intermediate product C
12H
9NO
6, structural formula:
Reaction yield 85%.
Infrared FT-IR (KBr), υ/cm
-1: 3495,3103,2995,2913,1771,1730,1623,1485,1442,1375,1263,1210,1073,994.
Nuclear-magnetism
1HNMR (CDCl
3) δ (ppm) 2.91 (s, 4H), 6.09 (S, 2H), 6.90 (d, 1H), 7.51 (S, 1H), 7.76 (d, 1H).
The 8g intermediate product is dissolved in the 100ml methylene dichloride, add the 10ml hexahydropyridine, stirring at room, thin-layer chromatography (TLC) tracks to and reacts completely, 2 hours reaction times, after reaction finishes, use the dilute hydrochloric acid of 1mol/L to wash three times, use anhydrous sodium sulfate drying, steam solvent, use the dehydrated alcohol recrystallization, obtain white solid product, be i.e. benzamide compounds C
13H
15NO
3, structural formula:
Productive rate 83%.
Infrared FT-IR (KBr), υ/cm
-1: 3071,3006,2926,2853,1607,1445,1282,1248,1077,1034,929,802;
Nuclear-magnetism
1HNMR (CDCl
3) δ (ppm) 1.51 (m, 6H), 3.43 (t, 4H), 6.00 (s, 2H), 6.80 (d, 1H), 6.89 (s, 1H), 6.92 (d, 1H).
Embodiment 2: the 10g piperinic acid is dissolved in the 150ml methylene dichloride, add the 5ml triethylamine, stirring and dissolving adds 20g trifluoroacetic acid succinimide ester, stirring at room, thin-layer chromatography (TLC) tracks to and reacts completely, and 4 hours reaction times is after reaction finishes, dilute hydrochloric acid with 1mol/L washs three times, use anhydrous sodium sulfate drying, steam solvent, obtain white powder intermediate product C
12H
9NO
6, structural formula:
Reaction yield 85%.
Infrared FT-IR (KBr), υ/cm
-1: 3495,3103,2995,2913,1771,1730,1623,1485,1442,1375,1263,1210,1073,994;
Nuclear-magnetism
1HNMR (CDCl
3) δ (ppm) 2.91 (s, 4H), 6.09 (s, 2H), 6.90 (d, 1H), 7.51 (s, 1H), 7.76 (d, 1H).
The 8g intermediate product is dissolved in the 100ml methylene dichloride, add 10ml morphine quinoline, stirring at room, thin-layer chromatography (TLC) tracks to and reacts completely, 4 hours reaction times, after reaction finishes, use the dilute hydrochloric acid of 1mol/L to wash three times, use anhydrous sodium sulfate drying, steam solvent, use the dehydrated alcohol recrystallization, obtain white solid product, be i.e. benzamide compounds C
12H
13NO
4, structural formula:
Productive rate 88%.
Infrared FT-IR (KBr), υ/cm
-1: 3452,3148,2955,1755,1713,1617,1494,1442,1365,1270,1149,1105,1032,933,857;
Nuclear-magnetism
1HNMR (CDCl
3) δ (ppm): 3.50 (t, 4H), 3.67 (t, 4H), 6.05 (s, 2H), 6.86 (d, 1H), 7.49 (s, 1H), 7.71 (d, 1H).
Embodiment 3: the 10g piperinic acid is dissolved in the 150ml methylene dichloride, add the 5ml triethylamine, stirring and dissolving adds 20g trifluoroacetic acid succinimide ester, stirring at room, thin-layer chromatography (TLC) tracks to and reacts completely, and 3 hours reaction times is after reaction finishes, dilute hydrochloric acid with 1mol/L washs three times, use anhydrous sodium sulfate drying, steam solvent, obtain white powder intermediate product C
12H
9NO
6, structural formula:
Reaction yield 85%.
Infrared FT-IR (KBr), υ/cm
-1: 3495,3103,2995,2913,1771,1730,1623,1485,1442,1375,1263,1210,1073,994;
Nuclear-magnetism
1HNMR (CDCl
3) δ (ppm) 2.91 (s, 4H), 6.09 (s, 2H), 6.90 (d, 1H), 7.51 (s, 1H), 7.76 (d, 1H).
The 8g intermediate product is dissolved in the 100ml methylene dichloride, add the 9ml tetramethyleneimine, stirring at room, thin-layer chromatography (TLC) tracks to and reacts completely, 3 hours reaction times, after reaction finishes, use the dilute hydrochloric acid of 1mol/L to wash three times, use anhydrous sodium sulfate drying, steam solvent, use the dehydrated alcohol recrystallization, obtain white solid product, be i.e. benzamide compounds C
12H
13NO
3, structural formula:
Productive rate 78%.
Nuclear-magnetism
1HNMR (CDCl
3) δ (ppm) 1.59 (m, 4H), 3.35 (t, 4H), 5.90 (s, 2H), 6.84 (d, 1H), 7.35 (s, 1H), 7.40 (d, 1H).
Embodiment 4: the 10g piperinic acid is dissolved in the 150ml methylene dichloride, add the 5ml triethylamine, stirring and dissolving adds 20g trifluoroacetic acid succinimide ester, stirring at room, thin-layer chromatography (TLC) tracks to and reacts completely, and 5 hours reaction times is after reaction finishes, dilute hydrochloric acid with 1mol/L washs three times, use anhydrous sodium sulfate drying, steam solvent, obtain white powder intermediate product C
12H
9NO
6, structural formula:
Reaction yield 85%.
Infrared FT-IR (KBr), υ/cm
-1: 3495,3103,2995,2913,1771,1730,1623,1485,1442,1375,1263,1210,1073,994;
Nuclear-magnetism
1HNMR (CDCl
3) δ (ppm) 2.91 (s, 4H), 6.09 (s, 2H), 6.90 (d, 1H), 7.51 (s, 1H), 7.76 (d, 1H).
The 8g intermediate product is dissolved in the 100ml methylene dichloride, add the 11ml piperazine, stirring at room, thin-layer chromatography (TLC) tracks to and reacts completely, 5 hours reaction times, after reaction finishes, use the dilute hydrochloric acid of 1mol/L to wash three times, use anhydrous sodium sulfate drying, steam solvent, use the dehydrated alcohol recrystallization, obtain white solid product, be i.e. benzamide compounds C
12H
14N
2O
3, structural formula:
Productive rate 82%.
Nuclear-magnetism
1HNMR (CDCl
3) δ (ppm) 2.0 (s, 1H), 2.85 (t, 4H), 3.32 (t, 4H), 5.90 (s, 2H), 6.83 (d, 1H), 7.36 (s, 1H), 7.41 (d, 1H).
Embodiment 5: 10g phendioxin-6-carboxylic acid is dissolved in the 170ml methylene dichloride stirring and dissolving, add the 7.5ml triethylamine, add 20g trifluoroacetic acid succinimide ester, stirring at room, thin-layer chromatography (TLC) tracks to and reacts completely, 2 hours reaction times, after reaction finishes, use the dilute hydrochloric acid of 1mol/L to wash three times, use anhydrous sodium sulfate drying, steam solvent, obtain white powder intermediate product C
13H
11NO
6, structural formula:
Reaction yield 83%.
Nuclear-magnetism
1HNMR (CDCl
3) δ (ppm): 2.74 (s, 4H), 4.36 (s, 4H), 6.89 (d, 2H), 7.53 (s, 1H), 7.59 (d, 1H).
The 8g intermediate product is dissolved in the 120ml methylene dichloride, add the 10ml hexahydropyridine, stirring at room, thin-layer chromatography (TLC) tracks to and reacts completely, 2 hours reaction times, after reaction finishes, use the dilute hydrochloric acid of 1mol/L to wash three times, use anhydrous sodium sulfate drying, steam solvent, use the dehydrated alcohol recrystallization, obtain white solid product, be i.e. benzamide compounds C
14H
17NO
3, structural formula:
Productive rate 82%.
Nuclear-magnetism
1HNMR (CDCl
3) δ (ppm) 1.50 (m, 6H), 3.36 (t, 4H), 4.36 (s, 4H), 6.84 (d, 1H), 7.35 (s, 1H), 7.58 (d, 1H).
Embodiment 6: 10g phendioxin-6-carboxylic acid is dissolved in the 170ml methylene dichloride, adds the 7.5ml triethylamine, stirring and dissolving, add 25g trifluoroacetic acid succinimide ester, stirring at room, thin-layer chromatography (TLC) tracks to and reacts completely, 4 hours reaction times, after reaction finishes, use the dilute hydrochloric acid of 1mol/L to wash three times, use anhydrous sodium sulfate drying, steam solvent, obtain white powder intermediate product C
13H
11NO
6, structural formula:
Reaction yield 83%.
Nuclear-magnetism
1HNMR (CDCl
3) δ (ppm): 2.74 (s, 4H), 4.36 (s, 4H), 6.89 (d, 2H), 7.53 (s, 1H), 7.59 (d, 1H).
The 8g intermediate product is dissolved in the 120ml methylene dichloride, add 10ml morphine quinoline, stirring at room, thin-layer chromatography (TLC) tracks to and reacts completely, 4 hours reaction times, after reaction finishes, use the dilute hydrochloric acid of 1mol/L to wash three times, use anhydrous sodium sulfate drying, steam solvent, use the dehydrated alcohol recrystallization, obtain white solid product, be i.e. benzamide compounds C
13H
15NO
4, structural formula:
Productive rate 89%.
Nuclear-magnetism
1HNMR (CDCl
3) δ (ppm): 3.47 (t, 4H), 3.67 (t, 4H), 4.37 (s, 2H), 6.84 (d, 1H), 7.36 (s, 1H), 7.61 (d, 1H).
Embodiment 7: 10g phendioxin-6-carboxylic acid is dissolved in the 170ml methylene dichloride, adds the 7.5ml triethylamine, stirring and dissolving, add 25g trifluoroacetic acid succinimide ester, stirring at room, thin-layer chromatography (TLC) tracks to and reacts completely, 3 hours reaction times, after reaction finishes, use the dilute hydrochloric acid of 1mol/L to wash three times, use anhydrous sodium sulfate drying, steam solvent, obtain white powder intermediate product C
13H
11NO
6, structural formula:
Reaction yield 83%.
Nuclear-magnetism
1HNMR (CDCl
3) δ (ppm): 2.74 (s, 4H), 4.36 (s, 4H), 6.89 (d, 2H), 7.53 (s, 1H), 7.59 (d, 1H).
The 8g intermediate product is dissolved in the 120ml methylene dichloride, add the 8ml tetramethyleneimine, stirring at room, thin-layer chromatography (TLC) tracks to and reacts completely, 3 hours reaction times, after reaction finishes, use the dilute hydrochloric acid of 1mol/L to wash three times, use anhydrous sodium sulfate drying, steam solvent, use the dehydrated alcohol recrystallization, obtain white solid product, be i.e. benzamide compounds C
13H
15NO
3, structural formula:
Productive rate 88%.
Nuclear-magnetism
1HNMR (CDCl
3) δ (ppm): 3.34 (t, 4H), 1.59 (t, 4H), 4.37 (s, 4H), 6.84 (d, 1H), 7.36 (s, 1H), 7.61 (d, 1H).
Embodiment 8: 10g phendioxin-6-carboxylic acid is dissolved in the 170ml methylene dichloride, adds the 7.5ml triethylamine, stirring and dissolving, add 25g trifluoroacetic acid succinimide ester, stirring at room, thin-layer chromatography (TLC) tracks to and reacts completely, 5 hours reaction times, after reaction finishes, use the dilute hydrochloric acid of 1mol/L to wash three times, use anhydrous sodium sulfate drying, steam solvent, obtain white powder intermediate product C
13H
11NO
6, structural formula:
Reaction yield 83%.
Nuclear-magnetism
1HNMR (CDCl
3) δ (ppm): 2.74 (s, 4H), 4.36 (s, 4H), 6.89 (d, 2H), 7.53 (s, 1H), 7.59 (d, 1H).
The 8g intermediate product is dissolved in the 120ml methylene dichloride, add the 11ml piperazine, stirring at room, thin-layer chromatography (TLC) tracks to and reacts completely, 5 hours reaction times, after reaction finishes, use the dilute hydrochloric acid of 1mol/L to wash three times, use anhydrous sodium sulfate drying, steam solvent, use the dehydrated alcohol recrystallization, obtain white solid product, be i.e. benzamide compounds C
13H
16N
2O
3, structural formula:
Productive rate 88%.
Nuclear-magnetism
1HNMR (CDCl
3) δ (ppm): 2.0 (s, 1H), 3.32 (t, 4H), 2.85 (t, 4H), 4.37 (s, 4H), 6.84 (d, 1H), 7.35 (s, 1H), 7.60 (d, 1H).
Claims (4)
1. benzamide compounds, its structural formula is
2. benzamide compounds, its structural formula is
3. benzamide compounds according to claim 1 and 2 is characterized in that: described R is
Any.
4. the preparation method of claim 1 or 2 described benzamide compounds is characterized in that may further comprise the steps:
(a) be 1: 15～1: 20 batching according to containing the mass/volume ratio of substituting group phenylformic acid with methylene dichloride, to contain the substituting group phenylformic acid is dissolved in the methylene dichloride, stirring and dissolving, according to containing the mass/volume ratio of substituting group phenylformic acid with triethylamine or pyridine is to add catalyst of triethylamine or pyridine in 2: 1～2: 1.5, obtains reaction mixture;
(b) in the reaction mixture of step (a) preparation,, add the trifluoroacetic acid succinimide ester according to containing substituting group phenylformic acid and trifluoroacetic acid succinimide ester mol ratio 1: 1～1: 3; Stirring reaction is 2～5 hours under the room temperature; Reaction process tracks to thin-layer chromatography and reacts completely, and after reaction finishes, the hydrochloric acid soln of reaction mixture with 1mol/L is washed three times, and anhydrous sodium sulfate drying steams solvent, obtains the reaction intermediate of white solid;
(c) intermediate product that step (b) is prepared is dissolved in trichloromethane or the dichloromethane solvent, the consumption of trichloromethane or methylene dichloride is 1: 12～1: 15 batching according to the mass/volume ratio of intermediate product and trichloromethane or methylene dichloride, after stirring, according to 8～11% of reaction soln cumulative volume, add the morphine quinoline, perhaps hexahydropyridine, perhaps tetramethyleneimine, perhaps pyrazine, stirring reaction is 2～5 hours under the room temperature, reaction process is followed the tracks of with thin-layer chromatography, after reaction finishes, hydrochloric acid soln with 1mol/L washs three times, and anhydrous sodium sulfate drying steams solvent, separate and purify, obtain benzamide compounds.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103804268A (en) * | 2013-12-29 | 2014-05-21 | 陕西师范大学 | Method for efficiently synthesizing functional enamine with high regioselectivity |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56103180A (en) * | 1980-01-22 | 1981-08-18 | Sumitomo Chem Co Ltd | Novel quinazoline derivative and its preparation |
| WO2007124348A2 (en) * | 2006-04-20 | 2007-11-01 | The Regents Of The University Of California | Pharmacological modulation of positive ampa receptor modulator effects on neurotrophin expression |
-
2011
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56103180A (en) * | 1980-01-22 | 1981-08-18 | Sumitomo Chem Co Ltd | Novel quinazoline derivative and its preparation |
| WO2007124348A2 (en) * | 2006-04-20 | 2007-11-01 | The Regents Of The University Of California | Pharmacological modulation of positive ampa receptor modulator effects on neurotrophin expression |
Non-Patent Citations (3)
| Title |
|---|
| 《J. Org. Chem.》 19791231 Francis J. McEvoy, et al. Alkylations and Acylations of alpha-Aryl-4-morpholineacetonitriles (Masked Acyl Anion Equivalents) and Their Use in 1,4-Additions 第4597-4603页 3 第44卷, 第25期 * |
| FRANCIS J. MCEVOY, ET AL.: "Alkylations and Acylations of α-Aryl-4-morpholineacetonitriles (Masked Acyl Anion Equivalents) and Their Use in 1,4-Additions", 《J. ORG. CHEM.》 * |
| PHILIPPE HERMANGE, ET AL.: "Ex Situ Generation of Stoichiometric and Substoichiometric 12CO and 13CO and Its Efficient Incorporation in Palladium Catalyzed Aminocarbonylations", 《J. AM. CHEM. SOC.》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103804268A (en) * | 2013-12-29 | 2014-05-21 | 陕西师范大学 | Method for efficiently synthesizing functional enamine with high regioselectivity |
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Effective date of registration: 20200423 Address after: 710304 room 10502, floor 5, unit 1, building 2, science and technology accelerator, No. 6, Qinling Avenue West, Caotang science and technology industrial base, Xi'an high tech Zone, Shaanxi Province Patentee after: Xi'an yutebang Pharmaceutical Technology Co., Ltd Address before: 710072 Xi'an friendship West Road, Shaanxi, No. 127 Patentee before: Northwestern Polytechnical University |