2,2-Dimethyl-1,3-dioxane-4,6-dione → HCID 68253433, compound

HRID 1853946Notes

Reaction equation

HRID 1853946 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[NH:11][CH2:12][CH2:13][C:14]([OH:16])=O.[CH3:17][C:18]1([CH3:26])[O:23][C:22](=[O:24])[CH2:21][C:20](=[O:25])[O:19]1>CN(C)C1C=CN=CC=1.ClCCl>[CH3:17][C:18]1([CH3:26])[O:23][C:22](=[O:24])[CH:21]([C:14](=[O:16])[CH2:13][CH2:12][NH:11][C:3]2[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=2[CH3:1])[C:20](=[O:25])[O:19]1

Participants

5

Reactant 2

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dione2×HCID 10105015HCID 10105015, compound

Product 1

HCID 68253433HCID 68253433, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(2-Methyl-5-nitro-phenylamino)-propionic acid [2.95 gm, 13.2 mmol], 2,2-dimethyl-1,3-dioxane-4,6-dione (Meldrum's acid (2.08 gm, 14.5 mmol), and 4-dimethylaminopyridine (DMAP) [2.42 gm, 198 mmol) in anhy. dichloromethane (70 ml) at 0° C. was added 1-(3-dimethylaminopropyl)-3-ethylcarboiimide hydrochloride (EDC.HCl) [3.04 gm, 158 mmol), and the resulting solution was stirred overnight at room temperature. The reaction mixture was washed (50 ml×4) with 5% potassium bisulfate (aq). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under vacuum, thereby affording crude 2,2-Dimethyl-5-[3-(2-methyl-5-nitro-phenylamino)propionyl]-[1,3]dioxane-4,6-dione (7), that was dissolved in 60 ml of ethyl acetate and refluxed for 4 hrs, The reaction mixture was cooled to room temperature and concentrated under vacuum. The crude product obtained was further purified by silica gel chromatography (eluent: 2% methanol in chloroform) to give desired produced i.e., 1-(2-Methyl-5-nitro-phenyl)-piperidine-2,4-dione [8] as yellow solid[Yield: 1.91 gm, 58.6%]

Workup

  1. washThe reaction mixture was washed (50 ml×4) with 5% potassium bisulfate (aq)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-07fecea607ca43d7b02bf0e5f403e4ad
Source dataset
uspto-grants-2015_02
Patent number
US08962637B2

Reaction notes

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