[ CAS No. 72432-10-1 ] {[proInfo.proName]}

Name: 72432-10-1|1-(4-Methoxybenzoyl)pyrrolidin-2-one|97%
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SKU: A890956
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Quality Control of [ 72432-10-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 72432-10-1 ]

SDS Specification

Alternatived Products of [ 72432-10-1 ]

Product Details of [ 72432-10-1 ]

CAS No. :	72432-10-1	MDL No. :	MFCD00153767
Formula :	C₁₂H₁₃NO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZXNRTKGTQJPIJK-UHFFFAOYSA-N
M.W :	219.24	Pubchem ID :	2196
Synonyms :	Ro 13-5057;Memodrin;Draganon;Ampamet;Sarpul

Calculated chemistry of [ 72432-10-1 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	62.45
TPSA :	46.61 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.52 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.55
Log Po/w (XLOGP3) :	1.58
Log Po/w (WLOGP) :	1.08
Log Po/w (MLOGP) :	1.59
Log Po/w (SILICOS-IT) :	1.85
Consensus Log Po/w :	1.53

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.27
Solubility :	1.17 mg/ml ; 0.00532 mol/l
Class :	Soluble
Log S (Ali) :	-2.17
Solubility :	1.48 mg/ml ; 0.00677 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.81
Solubility :	0.336 mg/ml ; 0.00153 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.26

Safety of [ 72432-10-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 72432-10-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 72432-10-1 ]
Downstream synthetic route of [ 72432-10-1 ]

[ 72432-10-1 ] Synthesis Path-Upstream 1~14

1
[ 616-45-5 ]
[ 100-09-4 ]
[ 72432-10-1 ]

Yield	Reaction Conditions	Operation in experiment
91%	With silica gel In tolueneReflux	Into a 250 mL four-necked flask, 150 mL of toluene, p-methoxybenzoic acid (34 g, 0.2 mol), α-pyrrolidone (17 g, 0.2 mol), silica (6 g, 10 mmol) were refluxed, and methanol was distilled off. . Methanol was evaporated and cooled to 15°C to precipitate a solid. Filter to obtain a solid cake. Dissolve with 95percent ethanol, decolorize the activated carbon, filter it while hot, crystallization after cold, filter and filter cake to obtain dried aniracetam finished product 39.5g. (Yield is 91percent)
79%	With zirconyl chloride octahydrate In chlorobenzene at 131℃; for 18 h; Dean-Stark	General procedure: In a typical reaction, a round-bottom flask equipped with a Dean-Stark apparatus, a magnetic stirring bar and temperature controller was charged with 2-pyrrolidone (5.8 mmol), palmitic acid (5.8 mmol), ZrOCl₂.8H₂O (0.58 mmol) and mesitylene (20 ml). When methyl palmitate was used as acylating agent, the Dean-Stark bridge was filled with 4Å molecular sieves to remove methanol from the reaction mixture. The set-up was flushed with gaseous nitrogen for 10 min before the onset of the reaction. The reaction vessel was then heated and kept for 18 h under reflux conditions.

Reference： [1] Patent: CN107840816, 2018, A, . Location in patent: Paragraph 0036-0049
[2] Tetrahedron Letters, 2018, vol. 59, # 17, p. 1646 - 1650
[3] Patent: EP2604592, 2014, B1, . Location in patent: Paragraph 0018

2
[ 201230-82-2 ]
[ 66897-25-4 ]
[ 72432-10-1 ]

Reference： [1] Angewandte Chemie - International Edition, 2015, vol. 54, # 35, p. 10239 - 10243[2] Angew. Chem., 2015, vol. 127, # 35, p. 10377 - 10381,5

3
[ 616-45-5 ]
[ 100-07-2 ]
[ 72432-10-1 ]

Reference： [1] Journal of the Chemical Society. Perkin Transactions 1, 2001, # 13, p. 1528 - 1531
[2] Patent: US4369139, 1983, A,
[3] Patent: US4369139, 1983, A,
[4] Patent: US4369139, 1983, A,

4
[ 64097-45-6 ]
[ 72432-11-2 ]
[ 100-07-2 ]
[ 72432-10-1 ]

Reference： [1] Patent: US4369139, 1983, A,

5
[ 66996-69-8 ]
[ 100-07-2 ]
[ 72432-10-1 ]

Reference： [1] Patent: US4369139, 1983, A,
[2] Patent: US4369139, 1983, A,

6
[ 616-45-5 ]
[ 123-11-5 ]
[ 72432-10-1 ]

Reference： [1] Organic Letters, 2012, vol. 14, # 17, p. 4646 - 4649

7
[ 7440-44-0 ]
[ 72432-14-5 ]
[ 72432-10-1 ]

Reference： [1] Patent: US4369139, 1983, A,

8
[ 100-07-2 ]
[ 72432-14-5 ]
[ 72432-10-1 ]

Reference： [1] Patent: US4369139, 1983, A,

9
[ 3195-95-7 ]
[ 72432-10-1 ]

Reference： [1] Patent: US4369139, 1983, A,

10
[ 616-45-5 ]
[ 105-13-5 ]
[ 72432-10-1 ]

Reference： [1] Chemical Science, 2018, vol. 9, # 21, p. 4756 - 4768

11
[ 69838-98-8 ]
[ 72432-10-1 ]

Reference： [1] Tetrahedron Letters, 1997, vol. 38, # 47, p. 8257 - 8260

12
[ 72432-13-4 ]
[ 72432-10-1 ]

Reference： [1] Patent: US4369139, 1983, A,

13
[ 3195-95-7 ]
[ 100-07-2 ]
[ 72432-10-1 ]

Reference： [1] Patent: US4369139, 1983, A,

14
[ 14468-90-7 ]
[ 100-07-2 ]
[ 72432-10-1 ]

Reference： [1] Patent: US4369139, 1983, A,

[ 72432-10-1 ] Synthesis Path-Downstream 1~46

1
[ 69838-98-8 ]
[ 72432-10-1 ]

Reference： [1]Tetrahedron Letters,1997,vol. 38,p. 8257 - 8260

2
[ 72432-10-1 ]
[ 616-45-5 ]
[ 100-09-4 ]

Reference： [1]Biological and Pharmaceutical Bulletin,1997,vol. 20,p. 869 - 873

3
[ 72432-10-1 ]
[ 72432-14-5 ]

Reference： [1]Biological and Pharmaceutical Bulletin,1997,vol. 20,p. 869 - 873

4
[ 616-45-5 ]
[ 100-07-2 ]
[ 72432-10-1 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In diethyl ether; water;	EXAMPLE 1 Preparation of 1-(p-methoxybenzoyl)-2-pyrrolidinone 40.0 g. of p-methoxybenzoyl chloride, 25.0 g. of 2-pyrrolidinone and 110 ml. of absolute diethyl ether are treated at between 0 C. and 10 C. while stirring with 52.5 ml. of triethylamine. The mixture is stirred at room temperature for a further 30 minutes and at reflux for 3 hours, then cooled down and treated at 2 C. with cold water. The insoluble constituents are filtered off under suction and washed with water and diethyl ether. The thus-obtained solid substance is recrystallized from alcohol after drying over phosphorus pentoxide. There is obtained 1-(p-methoxybenzoyl)-2-pyrrolidinone which melts at 121-122 C.
		EXAMPLE 5 Preparation of 1-(p-methoxybenzoyl)-2-pyrrolidinone 10 g. of 2-pyrrolidinone and 10 g. of p-methoxybenzoyl chloride are heated at 80-90 C. (internal temperature) in the absence of a solvent for 1 hour. The mixture is then left to cool down and is worked-up as described in Example 3. After recrystallization from alcohol, there is obtained 1-(p-methoxybenzoyl)-2-pyrrolidinone having a melting point of 120-121 C.
	With ammonium hydroxide; In diethyl ether;	EXAMPLE 3 Preparation of 1-(p-methoxybenzoyl)-2-pyrrolidinone 20 g. of p-methoxybenzoyl chloride and 20 g. of 2-pyrrolidinone are boiled at reflux in 20 ml. of diethyl ether for 16 hours and then diethyl ether, ice and 2-N aqueous ammonia are added to the mixture. The insoluble constituents are filtered off and washed ion-free with diethyl ether and water. The filter cake is dried and there is obtained 1-(p-methoxybenzoyl)-2-pyrrolidinone having a melting point of 119.5-120.5 C.

Reference： [1]Journal of the Chemical Society. Perkin Transactions 1 (2001),2001,p. 1528 - 1531
[2]Organic Letters,2019,vol. 21,p. 8205 - 8210
[3]Patent: US4369139,1983,A
[4]Patent: US4369139,1983,A
[5]Patent: US4369139,1983,A

5
[ 7440-44-0 ]
[ 72432-14-5 ]
[ 72432-10-1 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; In dichloromethane; toluene;	EXAMPLE 11 Preparation of 1-(p-methoxybenzoyl)-2-pyrrolidinone 20.0 g. of 4-(p-methoxybenzoylamino)butyric acid, 50 ml. of toluene and 9.2 ml. of thionyl chloride are heated at reflux for 2 hours and then the mixture is treated with decolorizing charcoal and evaporated. The residue is dissolved in methylene chloride and chromatographed over neutral aluminum oxide. The 1-(p-methoxybenzoyl)-2-pyrrolidinone, which is eluted with methylene chloride, is recrystallized from alcohol and has a melting point of 119-120 C.

Reference： [1]Patent: US4369139,1983,A

6
[ 3195-95-7 ]
[ 100-07-2 ]
[ 72432-10-1 ]

Yield	Reaction Conditions	Operation in experiment
	In N-methyl-acetamide; phosphorus pentaoxide; diethyl ether;	EXAMPLE 2 Preparation of 1-(p-methoxybenzoyl)-2-pyrrolidinone 20.2 g. of the sodium salt of 2-pyrrolidinone (prepared using sodium hydride) suspended in 270 ml. of dimethylformamide are added in four portions at -10 C. to a solution of 37.0 g. of p-methoxybenzoyl chloride in 50 ml. of dimethylformamide. Subsequently, the mixture is stirred at room temperature for 1 hour and then at 40 C. for 4 hours. The solvent is evaporated and the residue is treated with diethyl ether and with cold sodium bicarbonate solution. The insoluble crystalline constituents are filtered off, washed with water and diethyl ether and dried in vacuo over phosphorus pentoxide. There is obtained 1-(p-methoxybenzoyl)-2-pyrrolidinone having a melting point of 120-121 C.

Reference： [1]Patent: US4369139,1983,A

7
[ 64097-45-6 ]
[ 72432-11-2 ]
5-oxo-1-trimethylsilyl-3-pyrrolidinyl acetate [ No CAS ]
[ 100-07-2 ]
[ 72432-10-1 ]

Yield	Reaction Conditions	Operation in experiment
	With chloro-trimethyl-silane; sodium hydrogencarbonate; triethylamine;carbon palladium; In tetrahydrofuran; ethyl acetate;	EXAMPLE 9 Preparation of 1-(p-methoxybenzoyl)-2-pyrrolidinone 10.0 g. of 5-oxo-3-pyrrolidinyl acetate and 8.82 ml. of trimethylchlorosilane are dissolved in 100 ml. of absolute tetrahydrofuran and then 9.65 ml. of triethylamine are added at -5 C. to 0 C. The temperature is held at -5 C. to 0 C. for 1 hour, the mixture is then filtered under an argon atmosphere, the filtrate is evaporated and the residue is distilled in vacuo. There is obtained 5-oxo-1-trimethylsilyl-3-pyrrolidinyl acetate, having a boiling point of 110 C./0.07 mmHg. 12.5 g. of 5-oxo-1-trimethylsilyl-3-pyrrolidinyl acetate are placed in 30 ml. of absolute tetrahydrofuran and then 9.90 g. of p-methoxybenzoyl chloride dissolved in 10 ml. of absolute tetrahydrofuran are added dropwise at 0-10 C. The mixture is stirred at room temperature for 1 hour and at 70 C. for 1 hour and is then evaporated. The residue is dissolved in ethyl acetate and the ethyl acetate solution is washed with sodium chloride and sodium bicarbonate solution, dried over sodium sulfate and evaporated. 20 ml. of tetrahydrofuran and 20 ml. of saturated sodium bicarbonate solution are added to the residual viscous oil and the mixture obtained is then stirred at room temperature for 18 hours. The solvent mixture is decanted off and the residue is partitioned between water and methylene chloride. The organic phase is separated, dried over sodium sulfate and evaporated. The residual brown oil is chromatographed over silica gel (particle size 0.2-0.5 mm). The 1-(p-methoxybenzoyl)pyrrolin-2-one, which is eluted with benzene/diethyl ether (1:1) is recrystallized from alcohol and then has a melting point of 148-150 C. 150 mg. of 1-(p-methoxybenzoyl)pyrrolin-2-one are dissolved in 100 ml. of ethyl acetate and hydrogenated over 30 mg. of 5% palladium/carbon with hydrogen at atmospheric pressure and room temperature. After filtering off the catalyst and evaporating the solvent, there is obtained 1-(p-methoxybenzoyl)-2-pyrrolidinone.

Reference： [1]Patent: US4369139,1983,A

8
[ 100-07-2 ]
[ 72432-14-5 ]
[ 72432-10-1 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium hydroxide; phosphoric acid; In phosphorus pentaoxide; water; acetone; Petroleum ether; 4-amino-n-butyric acid;	EXAMPLE 10 Preparation of 1-(p-methoxybenzoyl)-2-pyrrolidinone 10.2 g. of p-methoxybenzoyl chloride are added at 30 C. in one portion while stirring well to 30.9 g. of 4-amino-butyric acid, 24.0 g. of sodium hydroxide and 300 ml. of ion-free water. After 2 hours, the mixture is acidified with 75 ml. of concentrated hydrochloric acid at a temperature below 10 C. The precipitate is filtered off, washed ion-free with water, dried in a drying oven at 65 C. over phosphorus pentoxide and then recrystallized from 45 ml. of acetone/low-boiling petroleum ether (3:1). There is obtained 4-(p-methoxybenzoylamino)butyric acid having a melting point of 120.5-122 C. 10 g. of phosphorus pentoxide and 6 ml. of orthophosphoric acid (at least 85%) are warmed with one another. 2.0 g. of 4-(p-methoxybenzoylamino)butyric acid are added at room temperature to the resulting solution. The mixture is warmed to 50 C. for 60 minutes, subsequently treated with ice and extracted with ethyl acetate. The organic phase is washed first with cold water, then with cold sodium bicarbonate solution and finally again with water and dried over sodium sulfate. The residue is triturated with diethyl ether and there is obtained 1-(p-methoxybenzoyl)-2-pyrrolidinone having a melting point of 120-122 C.

Reference： [1]Patent: US4369139,1983,A

9
[ 14468-90-7 ]
[ 100-07-2 ]
[ 72432-10-1 ]

Yield	Reaction Conditions	Operation in experiment
	In diethyl ether;	EXAMPLE 6 Preparation of 1-(p-methoxybenzoyl)-2-pyrrolidinone 24.4 g. of p-methoxybenzoyl chloride and 22.5 g. of 1-trimethylsilyl-2-pyrrolidinone are mixed and the mixture is stirred at room temperature for 10 minutes. Then, the resulting trimethylchlorosilane is distilled off under reduced pressure in an oil bath at 80 C. The residue is triturated with 100 ml. of diethyl ether. The mixture is filtered and the filter cake is recrystallized from ethanol. There is obtained 1-(p-methoxybenzoyl)-2-pyrrolidinone having a melting point of 120-121 C.

Reference： [1]Patent: US4369139,1983,A

10
[ 66996-69-8 ]
[ 100-07-2 ]
[ 72432-10-1 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium hydroxide; In water; ethyl acetate; benzene;	EXAMPLE 12 Preparation of 1-(p-methoxybenzoyl)-2-pyrrolidinone 276 mg. of lithium hydride (98%), 40 ml. of benzene and 4.2 g. of 2-methoxypyrroline are boiled at reflux for 2 hours under nitrogen and while stirring well. After cooling to 25 C., 6.6 g. of p-methoxybenzoyl chloride dissolved in 25 ml. of benzene are added and the resulting mixture is stirred under reflux for 2 hours and at room temperature for 16 hours. 100 ml. of ethyl acetate followed by 3.0 g. of lithium hydroxide (98%) dissolved in 25 ml. of water are added to the mixture at room temperature within 15 minutes. The organic phase is washed neutral with water, dried over sodium sulfate and evaporated under reduced pressure. After recrystallization from ethanol, there is obtained 1-(p-methoxybenzoyl)-2-pyrrolidinone having a melting point of 119-120 C.
	In ethanol; ethyl acetate; benzene;	EXAMPLE 13 Preparation of 1-(p-methoxybenzoyl)-2-pyrrolidinone 4.2 g. of 2-methoxypyrroline are dissolved in 25 ml. of benzene and treated at room temperature with 6.6 g. of p-methoxybenzoyl chloride dissolved in 30 ml. of benzene. The mixture is stirred at room temperature for 60 minutes and at reflux for 4 hours. 30 ml. of benzene are then added and the mixture is boiled at reflux for a further 24 hours. The volatile constituents are distilled off, the residue is taken up in ethanol, the mixture is concentrated, the residue is triturated with diethyl ether, filtered and the filter cake is taken up in ethyl acetate. The ethyl acetate solution is washed with sodium bicarbonate solution and water, dried over sodium sulfate and concentrated. The residue is sublimed in vacuo and there is obtained 1-(p-methoxybenzoyl)-2-pyrrolidinone having a melting point of 119-120 C.

Reference： [1]Patent: US4369139,1983,A
[2]Patent: US4369139,1983,A

11
p-methoxybenzoic acid pentachlorophenyl ester [ No CAS ]
[ 3195-95-7 ]
[ 72432-10-1 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; In N-methyl-acetamide; ethanol;	EXAMPLE 7 Preparation of 1-(p-methoxybenzoyl)-2-pyrrolidinone 7.0 g. of the sodium salt of 2-pyrrolidinone (prepared using sodium hydride) suspended in 120 ml. of dimethylformamide are added at -10 C. to a solution of 20.0 g. of p-methoxybenzoic acid pentachlorophenyl ester in 100 ml. of dimethylformamide. Subsequently, the mixture is stirred at room temperature for 1 hour and at 55 C. for 8 hours. The solvent is evaporated, the residue is treated with cold aqueous acetic acid solution and the mixture is extracted with ethyl acetate. The organic phase is washed with cold sodium bicarbonate solution and water, dried over sodium sulfate, filtered and evaporated. The residue is taken up in ethanol and stirred in an ice bath. The separated crystals are filtered off and there is obtained 1-(p-methoxybenzoyl)-2-pyrrolidinone having a melting point of 119-120 C.

Reference： [1]Patent: US4369139,1983,A

12
etheric diazomethane [ No CAS ]
[ 72432-13-4 ]
[ 72432-10-1 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran;	150 mg. of 1-(p-hydroxybenzoyl)-2-pyrrolidinone are dissolved in 7 ml. of absolute tetrahydrofuran and then etheric diazomethane solution is added. The solvents are distilled off, the residue is triturated with diethyl ether and the mixture is filtered. There is obtained 1-(p-methoxybenzoyl)-2-pyrrolidinone which melts at 117.5-119 C. after sublimation.

Reference： [1]Patent: US4369139,1983,A

13
[ 616-45-5 ]
[ 123-11-5 ]
[ 72432-10-1 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 4646 - 4649

14
[ 616-45-5 ]
[ 100-09-4 ]
[ 72432-10-1 ]

Yield	Reaction Conditions	Operation in experiment
91%	With silica gel; In toluene;Reflux;	Into a 250 mL four-necked flask, 150 mL of toluene, p-methoxybenzoic acid (34 g, 0.2 mol), alpha-pyrrolidone (17 g, 0.2 mol), silica (6 g, 10 mmol) were refluxed, and methanol was distilled off. . Methanol was evaporated and cooled to 15C to precipitate a solid. Filter to obtain a solid cake. Dissolve with 95% ethanol, decolorize the activated carbon, filter it while hot, crystallization after cold, filter and filter cake to obtain dried aniracetam finished product 39.5g. (Yield is 91%)
84.6%	With phenylboronic acid; In benzene; for 16h;Reflux; Green chemistry;	To the flask was added chlorobenzene (300 ml), p-methoxybenzoic acid (30.4 g),2-pyrrolidone (17.0 g) and phenylboronic acid (2.4 g),After the addition, heating and refluxing for 16 hours,The produced water is removed by a reflux dehydration device,Fully reacted; cooled, first filtered to obtain a solid filter cake,Then dissolved in ethanol and decolorized with activated carbon.After hot filtration, cool and crystallize, and finally filter,Take the filter cake,The target product aniracetam is obtained by drying under reduced pressure.(37.1 g), yield 84.6%.
79%	With zirconyl chloride octahydrate; In chlorobenzene; at 131℃; for 18h;Dean-Stark;	General procedure: In a typical reaction, a round-bottom flask equipped with a Dean-Stark apparatus, a magnetic stirring bar and temperature controller was charged with 2-pyrrolidone (5.8 mmol), palmitic acid (5.8 mmol), ZrOCl2.8H2O (0.58 mmol) and mesitylene (20 ml). When methyl palmitate was used as acylating agent, the Dean-Stark bridge was filled with 4A molecular sieves to remove methanol from the reaction mixture. The set-up was flushed with gaseous nitrogen for 10 min before the onset of the reaction. The reaction vessel was then heated and kept for 18 h under reflux conditions.

94 g (0.79 mol) of thionyl chloride and 30 g (0.197) of 4-methoxybenzoic acid was measured into a 250 mL round-bottom flask fitted with a stirrer, thermometer and reflux condenser. Subsequently, the mixture was heated to a boil (76C) and maintained at that temperature for three hours upon stirring; subsequently, the unreacted thionyl chloride was distilled off in vacuum. The distillation residue was cooled to 50C and dissolved in 120 mL of toluene. 26.0 g (0.256 mol) of triethylamine and 17.6 g (0.207 mol) of 2-pyrrolidone was added to the toluene solution. The reaction mixture was heated to a boil (110C) and maintained under reflux for 2.5 hours; subsequently, it was cooled to 20C and 60 mL of water was added. The precipitate of crude aniracetam was filtered off, washed three times with 50 mL of water and dried. 34.9 g of a crude product was obtained with a yield of 80%.

Reference： [1]Patent: CN107840816,2018,A .Location in patent: Paragraph 0036-0049
[2]Patent: CN109651222,2019,A .Location in patent: Paragraph 0058; 0059; 0061; 0062; 0063-0073
[3]Tetrahedron Letters,2018,vol. 59,p. 1646 - 1650
[4]Patent: EP2604592,2014,B1 .Location in patent: Paragraph 0018

15
[ 1120-64-5 ]
[ 72432-10-1 ]
(2-acetoxyethylamino)aniracetam [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 9816 - 9819

16
[ 201230-82-2 ]
[ 66897-25-4 ]
[ 72432-10-1 ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 10239 - 10243
Angew. Chem.,2015,vol. 127,p. 10377 - 10381,5

17
[ 616-45-5 ]
[ 105-13-5 ]
[ 72432-10-1 ]

Reference： [1]Chemical Science,2018,vol. 9,p. 4756 - 4768

18
[ 72432-10-1 ]
[ 407-25-0 ]
(Z)-3-(1-chloro-2,2,2-trifluoroethylidene)-1-(4-methoxybenzoyl)pyrrolidin-2-one [ No CAS ]
(E)-3-(1-chloro-2,2,2-trifluoroethylidene)-1-(4-methoxybenzoyl)pyrrolidin-2-one [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2018,vol. 360,p. 2178 - 2182

19
[ 616-45-5 ]
[ 78823-41-3 ]
[ 72432-10-1 ]

Yield	Reaction Conditions	Operation in experiment
31.8 g	In dichloromethane;Reflux;	Dichloromethane (250 ml), p-methoxybenzoic acid (30.4 g), pyridine (64.3 g) were added to the flask, and pivaloyl chloride (25.3 g) was slowly added dropwise under ice-cooling, and the mixture was refluxed and heated to reflux. Stirring reaction for 2 hours; then, adding 2-pyrrolidone (25.5g), heating under reflux, stirring the reaction for 6~24 hours until the reaction is complete, washing with water, washing with sodium carbonate aqueous solution, drying, concentrating, dissolving with ethanol, decolorizing activated carbon The mixture was filtered while hot, cooled and crystallized, filtered again, and the cake was taken and dried under reduced pressure to obtain the desired product aniacetam (31.8 g) in a yield of 72.5%.

Reference： [1]Patent: CN109503451,2019,A .Location in patent: Paragraph 0018; 0042-0055

Yield	Reaction Conditions	Operation in experiment
63%	With manganese(II) triflate; 4,4'-diamino-2,2'-bipyridyl; dihydrogen peroxide; In acetone; at 20℃; for 1h;	General procedure: 5.59 mg (0.03 mmol) of 4,4'-diamino-2,2'-bipyridine (Ligand), 5.30 mg (0.015 mmol) of manganese (II) triflate (Mn(OTf) 2),1.5 mL of acetone was added to the reaction tube, and the reaction was stirred at 70 C for 10 min.Cool to room temperature and add 49.57 mg (0.5 mmol) of 2-piperidone.Then, 250 muL of 30% by mass of hydrogen peroxide was diluted with 0.5 mL of acetone and then added to the reaction tube through a flow injection pump for 60 minutes.After the addition, saturated sodium sulfite was added to the reaction solution to quench the remaining hydrogen peroxide.Extraction with ethyl acetate gave 1,2-dipiperidone in a yield of 98%.

21
[ 72432-10-1 ]
[ 72432-13-4 ]