CN114671796A - Method for synthesizing N-alkyl phthalimide through photocatalysis - Google Patents

Method for synthesizing N-alkyl phthalimide through photocatalysis Download PDF

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CN114671796A
CN114671796A CN202210429375.4A CN202210429375A CN114671796A CN 114671796 A CN114671796 A CN 114671796A CN 202210429375 A CN202210429375 A CN 202210429375A CN 114671796 A CN114671796 A CN 114671796A
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ethyl acetate
alkylphthalimide
phthalimide
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奚建英
方烨汶
张莉
金小平
陈斌
张宗勇
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Ningbo University of Technology
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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide

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Abstract

The invention provides a method for synthesizing N-alkyl phthalimide by photocatalysis, which comprises the following steps: s1: to a reaction tube with a stirrer was added N-alkenylphthalimide and a photosensitizer Ir [ dF (CF)3)ppy]2(dtbbpy)PF6Then adding a radical precursor silicon alkyl to the reaction tube; s2: adding dimethyl sulfoxide into the reaction tube, evacuating the reaction tube, exchanging nitrogen, placing the reaction tube under a 9W blue light LED lamp for irradiation, stirring, diluting the reaction solution with ethyl acetate and water, and extracting with ethyl acetate; s3: combining the organic phases obtained by extraction, drying with anhydrous sodium sulfate, filtering again to obtain an organic phase solution, and removing the solvent by a rotary evaporator; then the mixed solution of petroleum ether and ethyl acetate is used as eluent to carry out column chromatography separation, and finally the product N-alkyl phthalimide is obtained by distillation of a rotary evaporator. The method can be used for efficiently preparing the N-alkyl phthalimide, and has high production efficiency and few byproducts.

Description

Method for synthesizing N-alkyl phthalimide through photocatalysis
Technical Field
The invention relates to the field of photocatalytic synthesis, in particular to a method for synthesizing N-alkyl phthalimide through photocatalysis.
Background
Primary amines are a basic and important class of organic compounds, and are also important intermediates in chemical reactions. Hydrolysis of N-alkylphthalimides is one of the important processes for the synthesis of primary amines and is known as the Gabriel amine synthesis. The synthesis method has no side reaction problem of secondary and tertiary amine, so that the method can be used for synthesizing primary amine with higher purity. In the process for preparing N-substituted phthalimides, the conventional method commonly used is to react phthalimide with a halogenated hydrocarbon under the action of a base (e.g., reaction formula (1)). However, this synthesis method is suitable for primary halogenated hydrocarbons having high reactivity, and is not efficient in secondary halogenated hydrocarbons and involves many side reactions.
Figure BDA0003609487170000011
The free radical addition reaction of N-alkenyl phthalimide as an acceptor provides a good alternative strategy to the low efficiency between secondary halides and phthalimides. For example, synthesis of unnatural amino acid derivatives can be achieved using an olefin as a radical precursor under iron-catalyzed conditions (e.g., equation (2)). In addition, an addition reaction is carried out by using aldehyde as a radical precursor and generating an acyl radical and N-alkenylphthalimide through the cleavage of a C-H bond under the catalysis of tetrabutylammonium decatungstate (TBADT) (as shown in the reaction formula (3)). The catalytic system can generate C-H bond breakage to generate alkyl free radical and perform addition reaction for the hydrogen at benzyl position and tertiary position, but the efficiency is general.
Figure BDA0003609487170000021
In view of the universality and universality of the Gabriel amine synthesis method in primary amine synthesis, the development of a high-efficiency N-alkylphthalimide synthesis method still has important significance, and particularly the N-alkylphthalimide synthesis method which is mild in reaction conditions, simple in operation, good in universality and high in efficiency is more important.
Disclosure of Invention
The invention aims to solve the technical problem of providing a method for synthesizing N-alkyl phthalimide by photocatalysis, so as to solve the problems of low reaction efficiency, more byproducts, and poor universality and universality in the conventional reaction.
In order to solve the problems, the invention provides a method for synthesizing N-alkyl phthalimide by photocatalysis, which comprises the following specific steps:
s1: adding N-alkenyl phthalimide and photosensitizer Ir [ dF (CF) into a reaction tube with a stirrer3)ppy]2(dtbbpy)PF6Then adding a radical precursor silicon alkyl to the reaction tube;
s2: adding dimethyl sulfoxide into the reaction tube obtained after the operation of the step S1, evacuating the reaction tube, replacing nitrogen, placing the reaction tube under a 9W blue LED lamp for irradiation, stirring, diluting the reaction solution with ethyl acetate and water, and extracting with ethyl acetate;
s3: combining the organic phases obtained by the extraction in the step S2, drying the combined organic phases by using anhydrous sodium sulfate, filtering the combined organic phases again to obtain an organic phase solution, and removing the solvent by using a rotary evaporator; then the mixed solution of petroleum ether and ethyl acetate is used as eluent to carry out column chromatography separation, and finally the product N-alkyl phthalimide is obtained by distillation of a rotary evaporator.
Preferably, in step S1, the N-alkenylphthalimide is reacted with Ir [ dF (CF)3)ppy]2(dtbbpy)PF6In a molar ratio of 1: (0.01-0.03).
Preferably, in step S1, the molar ratio of N-alkenylphthalimide to radical precursor alkylsilane is 1: (1.5-2.5).
Preferably, in step S1, the alkylsilane serving as the radical precursor is one of chloropropylbis (catechol) silicate-18-crown ether-6-potassium, cyclohexylbis (catechol) silicate-18-crown ether-6-potassium and ethylbis (catechol) silicate-18-crown ether-6-potassium.
Preferably, in step S2, the stirring conditions are: stirred at room temperature for 24 hours.
Preferably, in the step S1 and the step S2, the molar ratio of the N-alkenyl phthalimide to the dimethyl sulfoxide is 1: (400-450).
Preferably, in the step S3, the volume ratio of the petroleum ether to the ethyl acetate in the mixed solution of the petroleum ether and the ethyl acetate is 10: 1.
Preferably, in the step S3, the length of the silica gel column in the column chromatography separation is 10 cm.
Preferably, the reaction formula of the method is as follows:
Figure BDA0003609487170000031
the beneficial effects of the invention are: the invention relates to a method for synthesizing N-alkyl phthalimide by photocatalysis, and provides a novel method for modularizing and synthesizing N-alkyl phthalimide; the invention has the advantages of wide substrate application range, good functional group compatibility, mild and efficient reaction conditions and simple and convenient operation; the invention provides a novel method for synthesizing N-alkyl phthalimide by taking high-valence organic silicon as a free radical precursor and N-alkenyl phthalimide as a free radical acceptor under the mild visible light irradiation condition without alkali and an additional reducing agent, and the method has the advantages of low preparation cost, simple condition, higher universality and universality, fewer reaction byproducts, high reaction efficiency and higher popularization value and commercial value.
Detailed Description
The technical solutions of the present invention will be described clearly and completely below, and it should be apparent that the described embodiments are some, but not all, embodiments of the present invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The invention provides the following method for obtaining N-alkyl phthalimide by photocatalytic synthesis:
the invention provides a method for synthesizing N-alkyl phthalimide by photocatalysis, which comprises the following steps:
s1: to a reaction tube with a stirrer was added N-alkenylphthalimide and a photosensitizer Ir [ dF (CF)3)ppy]2(dtbbpy)PF6Then adding a radical precursor silicon alkyl to the reaction tube;
s2: adding dimethyl sulfoxide into the reaction tube obtained after the operation of the step S1, evacuating the reaction tube, replacing nitrogen, placing the reaction tube under a 9W blue LED lamp for irradiation, stirring, diluting the reaction solution with ethyl acetate and water, and extracting with ethyl acetate;
s3: combining the organic phases obtained by the extraction in the step S2, drying the combined organic phases by using anhydrous sodium sulfate, filtering the combined organic phases again to obtain an organic phase solution, and removing the solvent by using a rotary evaporator; then the mixed solution of petroleum ether and ethyl acetate is used as eluent to carry out column chromatography separation, and finally the product N-alkyl phthalimide is obtained by distillation of a rotary evaporator.
Preferably, in step S1, the N-alkenylphthalimide is reacted with Ir [ dF (CF)3)ppy]2(dtbbpy)PF6In a molar ratio of 1: (0.01-0.03).
Preferably, in step S1, the molar ratio of N-alkenylphthalimide to radical precursor silane is 1: (1.5-2.5).
Preferably, in step S1, the alkyl silicon as the radical precursor is one of chloropropyl bis (catechol) silicate-18-crown ether-6-potassium, cyclohexyl bis (catechol) silicate-18-crown ether-6-potassium and ethyl bis (catechol) silicate-18-crown ether-6-potassium.
Preferably, in step S2, the stirring conditions are: stirred at room temperature for 24 hours.
Preferably, in the step S1 and the step S2, the molar ratio of N-alkenyl phthalimide to dimethyl sulfoxide is 1: (400-450).
Preferably, in the step S3, the volume ratio of the petroleum ether to the ethyl acetate in the mixed solution of the petroleum ether and the ethyl acetate is 10: 1.
Preferably, in the step S3, in the column chromatography separation, the length of the silica gel column is 10 cm.
Preferably, the reaction formula of the process is as follows:
Figure BDA0003609487170000051
the above method is described below with reference to specific data:
example one
S1: put magneton into reaction tube, add Ir [ dF (CF)3)ppy]2(dtbbpy)PF6(4.5mg,0.004mmol,0.02equiv), ethyl 2- (N-phthalimide) acrylate (49.0mg,0.2mmol,1.0 equiv); placing the reaction tube into a glove box, and weighing chloropropylbis (catechol) silicate-18-crown ether-6-potassium complex (249.8mg,0.4mmol,2.0equiv) in the glove box;
s2: the reaction tube was stoppered with a rubber stopper, dried dimethyl sulfoxide (6mL) was added under nitrogen, and the rubber stopper was sealed with a sealing film. Irradiating the reaction tube under a 9W blue light LED lamp, stirring at room temperature for 24h, stopping the illumination reaction, adding 6mL of water into the reaction solution, and extracting with ethyl acetate (4X 10 mL);
s3: the organic phases were combined, washed with 5mL of saturated brine, dried over anhydrous sodium sulfate, filtered, the solvent was removed by rotary evaporation of the filtrate, and the residue was washed with a mixture of petroleum ether and ethyl acetate (V)Petroleum ether:VEthyl acetate10: 1) the target product 45.9mg is obtained by flash column chromatography, the yield is 71 percent, and the product is faint yellow viscous liquid. The analytical data are as follows:
1H NMR(500MHz,CDCl3):δ7.88-7.86(m,2H),7.77-7.75(m,2H),4.83(dd,J=10.4Hz,5.2Hz,1H),4.23-4.16(m,2H),3.51-3.48(m,2H),2.32-2.21(m,2H),1.88-1.74(m,2H),1.51-1.41(m,2H),1.22(t,J=7.2Hz,3H);13C NMR(125MHz,CDCl3):δ169.1,167.7,134.2,131.7,123.6,61.9,52.0,44.5,31.8,27.9,23.6,14.1;HRMS(ESI)calculated for C16H19ClNO4[M+H]+324.1003,found 324.1007.
the general reaction formula of the above example is as follows:
Figure BDA0003609487170000061
example two
S1: put magneton into reaction tube, add Ir [ dF (CF)3)ppy]2(dtbbpy)PF6(4.5mg,0.004mmol,0.02equiv), ethyl 2- (N-phthalimide) acrylate (49.0mg,0.2mmol,1.0 equiv); the reaction tube was placed in a glove box, and cyclohexylbis (catechol) silicate-18-crown-6-potassium complex (252.0mg,0.4mmol,2.0equiv) was weighed in the glove box;
s2: the reaction tube was stoppered with a rubber stopper, dried dimethyl sulfoxide (6mL) was added under nitrogen, and the rubber stopper was sealed with a sealing film. Irradiating the reaction tube under a 9W blue light LED lamp, stirring at room temperature for 24h, stopping the illumination reaction, adding 6mL of water into the reaction solution, and extracting with ethyl acetate (4X 10 mL);
s3: the organic phase was combined, washed with 5mL of saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was evaporated to remove the solvent, and then mixed with a mixture of petroleum ether and ethyl acetate (V)Petroleum ether:VEthyl acetate10: 1) the target product 54.6mg is obtained by flash column chromatography, the yield is 83 percent, and the product is light yellow viscous liquid. The analytical data are as follows:
1H NMR(500MHz,CDCl3):δ7.87-7.84(m,2H),7.75-7.72(m,2H),4.95(dd,J=11.5Hz,4.4Hz,1H),4.21-4.14(m,2H),2.29-2.23(m,1H),2.04-1.98(m,1H),1.87(d,J=12.7Hz,1H),1.71-1.60(m,4H),1.20(t,J=7.1Hz,3H),1.15-1.09(m,4H),1.02-0.97(m,1H),0.95-0.86(m,1H);13C NMR(125MHz,CDCl3):δ169.8,167.7,134.1,131.8,123.4,61.7,50.1,35.9,34.3,33.7,31.6,26.3,26.1,25.8,14.0.
the general reaction formula of example 2 above is as follows:
Figure BDA0003609487170000071
EXAMPLE III
S1: a magneton is put into the reaction tube, and Ir [ dF (CF) is added3)ppy]2(dtbbpy)PF6(4.5mg,0.004mmol,0.02equiv), 1- (N-phthalimide) styrene (49.0mg,0.2mmol,1.0 equiv); the reaction tube was placed in a glove box, and ethyl bis (catechol) silicate-18-crown ether-6-potassium complex (230.4mg,0.4mmol,2.0equiv) was weighed in the glove box;
s2: the reaction tube was stoppered with a rubber stopper, dried dimethyl sulfoxide (6mL) was added under nitrogen, and the rubber stopper was sealed with a sealing film. Irradiating the reaction tube under a 9W blue light LED lamp, stirring at room temperature for 24h, stopping the illumination reaction, adding 6mL of water into the reaction solution, and extracting with ethyl acetate (4X 10 mL);
s3: the organic phases were combined and washed with 5mL of saturated brine, the organic phase was dried over anhydrous sodium sulfate and filtered, the solvent was removed by rotary evaporation of the filtrate, and then a mixture of petroleum ether and ethyl acetate (V)Petroleum ether:VEthyl acetate10: 1) the target product 37.4mg is obtained by flash column chromatography, the yield is 67 percent, and the product is pale yellow viscous liquid. The analytical data are as follows:
1H NMR(500MHz,CDCl3):δ7.71-7.70(m,2H),7.59-7.58(m,2H),7.46(d,J=7.8Hz,2H),7.25-7.22(m,2H),7.18-7.15(m,1H),5.28-5.25(m,1H),2.53-2.46(m,1H),2.18-2.11(m,1H),1.31-1.22(m,2H),0.88(t,J=7.3Hz,3H);13C NMR(125MHz,CDCl3):δ168.4,139.8,133.9,131.8,128.4,128.1,127.7,123.1,54.6,32.9,20.2,13.7.
the general reaction formula of example 3 above is as follows:
Figure BDA0003609487170000081
through the preparation reactions and the product tests of the above examples 1-3, the invention further illustrates that the invention provides a new method for synthesizing N-alkylphthalimide by using high-valence organosilicon as a radical precursor and N-alkenylphthalimide as a radical acceptor under the mild visible light irradiation condition without alkali and an additional reducing agent, and simultaneously solves the problems of low yield and more byproducts in the conventional preparation method.
Although the present disclosure has been described above, the scope of the present disclosure is not limited thereto. Those skilled in the art can make various changes and modifications without departing from the spirit and scope of the present disclosure, and such changes and modifications will fall within the scope of the present invention.

Claims (9)

1. A method for photocatalytic synthesis of N-alkylphthalimide, comprising the steps of:
s1: to a reaction tube with a stirrer was added N-alkenylphthalimide and a photosensitizer Ir [ dF (CF)3)ppy]2(dtbbpy)PF6Then adding a radical precursor silicon alkyl to the reaction tube;
s2: adding dimethyl sulfoxide into the reaction tube operated in the step S1, evacuating the reaction tube, exchanging nitrogen, placing the reaction tube under a 9W blue LED lamp for irradiation, stirring, diluting the reaction solution with ethyl acetate and water, and extracting with ethyl acetate;
s3: combining the organic phases obtained by the extraction in the step S2, drying the combined organic phases by using anhydrous sodium sulfate, filtering the combined organic phases again to obtain an organic phase solution, and removing the solvent by using a rotary evaporator; then the mixed solution of petroleum ether and ethyl acetate is used as eluent to carry out column chromatography separation, and finally the product N-alkyl phthalimide is obtained by distillation of a rotary evaporator.
2. The photocatalytic synthesis of N-alkylphthalimide according to claim 1 wherein: in the step S1, the N-alkenyl phthalimide is reacted with Ir [ dF (CF)3)ppy]2(dtbbpy)PF6In a molar ratio of 1: (0.01-0.03).
3. The photocatalytic synthesis of N-alkylphthalimide according to claim 1 wherein: in the step S1, the molar ratio of the N-alkenyl phthalimide to the radical precursor alkyl silicon is 1 (1.5-2.5).
4. The photocatalytic synthesis method of N-alkylphthalimide as claimed in claim 1 wherein: in the step S1, the alkyl silicon as the radical precursor is one of chloropropyl bis (catechol) silicate-18-crown ether-6-potassium alloy, cyclohexyl bis (catechol) silicate-18-crown ether-6-potassium alloy, and ethyl bis (catechol) silicate-18-crown ether-6-potassium alloy.
5. The photocatalytic synthesis method of N-alkylphthalimide as claimed in claim 1 wherein: in step S2, the stirring conditions are as follows: stirred at room temperature for 24 hours.
6. The photocatalytic synthesis of N-alkylphthalimide according to claim 1 wherein: in the step S1 and the step S2, the molar ratio of N-alkenyl phthalimide to dimethyl sulfoxide is 1: (400-450).
7. The photocatalytic synthesis of N-alkylphthalimide according to claim 1 wherein: in the step S3, the volume ratio of petroleum ether to ethyl acetate in the mixed solution of petroleum ether and ethyl acetate is 10: 1.
8. The photocatalytic synthesis method of N-alkylphthalimide as claimed in claim 1 wherein: in the step S3, the length of the silica gel column is 10cm in the column chromatography separation.
9. The photocatalytic synthesis process for an N-alkylphthalimide as claimed in any one of claims 1 to 8, wherein the reaction scheme of the process is as follows:
Figure FDA0003609487160000021
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