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Chemical Structure| 2353-44-8 Chemical Structure| 2353-44-8

Structure of 3-Aminopiperidine-2,6-dione
CAS No.: 2353-44-8

Chemical Structure| 2353-44-8

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Product Details of [ 2353-44-8 ]

CAS No. :2353-44-8
Formula : C5H8N2O2
M.W : 128.13
SMILES Code : NC1CCC(=O)NC1=O
MDL No. :MFCD11506223
InChI Key :NPWMTBZSRRLQNJ-UHFFFAOYSA-N
Pubchem ID :134508

Safety of [ 2353-44-8 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P301+P330+P331-P303+P361+P353-P363-P304+P340-P310-P321-P260-P264-P280-P305+P351+P338-P405-P501
Class:8
UN#:3259
Packing Group:

Application In Synthesis of [ 2353-44-8 ]

* 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.

  • Downstream synthetic route of [ 2353-44-8 ]

[ 2353-44-8 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 74530-56-6 ]
  • [ 2353-44-8 ]
  • 3-(2,4-dioxopyrrolidin-1-yl)piperidine-2,6-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N,N-dimethyl-formamide; at 35 - 125℃; for 7.0h;Inert atmosphere; Reflux; Under a nitrogen atmosphere, 140 g of N,N-dimethylformamide and 12.8 g (0.1 mol) were placed in a 500 ml four-necked flask equipped with a stirring, thermometer and air condenser.3-aminopiperidine-2,6-dione,21.5 g (0.11 mol) of 1-chloroacetoacetic acid tert-butyl ester,40 g of potassium carbonate, stirred at 35 to 40 C for 4 hours,The reaction was stirred at 120 to 125 C for 3 hours.Distilling off the tert-butanol formed by the amidation reaction; cooling to 40 C,21.5 (0.11 mol) of 2-bromo-4-nitro-n-butyraldehyde was added, and the reaction was stirred at 40 to 45 C for 5 hours.Filtered, the filter cake was washed with 40 g of N,N-dimethylformamide.Combine the filtrate,Distillation of N,N-dimethylformamide, addition of 90 g of isopropanol, recrystallization,26.9 g of 3-(7-nitro-3-oxo-1H-isoindol-2-yl)piperidine were obtained -2,6-dione, yield 93.0%, liquid phase purity 99.2%.
  • 2
  • [ 51108-29-3 ]
  • [ 2353-44-8 ]
  • 2-(2,6-dioxopiperidin-3-yl)-4-fluoro-2,3-dihydro-1H-isoindole-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With anhydrous potassium acetate; acetic acid; for 8h;Reflux; Inert atmosphere; To a stirred solution of 1 (4-fluoroisoindoline-1,3-dione) (10.0g, 60.6mmol) in acetic acid (100mL) was added with potassium acetate (7.1g, 72.7mmol) and 3-aminopiperidine-2,6-dione (5.2g, 40.4mmol). The mixture was heated to reflux and stirred for 8h and then cooled to room temperature. Water was added in the mixture and precipitation occurred. The solid was collected and dried after filtration to give the title compound (10g, 87% yield) as a gray solid. The product was directly used in the next step without further purification. 1H NMR (400MHz, Methanol-d4) δ 7.95-7.85 (m, 1H), 7.76 (d, J=7.3Hz, 1H), 7.58 (t, J=8.8Hz, 1H), 5.17 (dd, J=12.6, 5.5Hz, 1H), 2.96-2.84 (m, 1H), 2.82-2.67 (m, 2H), 2.22-2.12 (m, 1H). MS (ESI) 277.1 [M+H]+.
87% With anhydrous potassium acetate; acetic acid; for 8h;Reflux; Inert atmosphere; To a stirred solution of 1 (4-fluoroisoindoline-1,3-dione) (10.0g, 60.6mmol) in acetic acid (100mL) was added with potassium acetate (7.1g, 72.7mmol) and 3-aminopiperidine-2,6-dione (5.2g, 40.4mmol). The mixture was heated to reflux and stirred for 8h and then cooled to room temperature. Water was added in the mixture and precipitation occurred. The solid was collected and dried after filtration to give the title compound (10g, 87% yield) as a gray solid. The product was directly used in the next step without further purification. 1H NMR (400MHz, Methanol-d4) δ 7.95-7.85 (m, 1H), 7.76 (d, J=7.3Hz, 1H), 7.58 (t, J=8.8Hz, 1H), 5.17 (dd, J=12.6, 5.5Hz, 1H), 2.96-2.84 (m, 1H), 2.82-2.67 (m, 2H), 2.22-2.12 (m, 1H). MS (ESI) 277.1 [M+H]+.
 

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[ 2353-44-8 ]

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