Dimethylformamide → 1,3,3-Trimethylpiperazine-2,5-dione

HRID 1437249Notes

Reaction equation

HRID 1437249 reaction equation
N1CCCC[CH2:2]1.C(O[C:10](=O)[CH2:11][N:12]([C:14](=[O:16])C)C)C.[CH3:18][N:19]([CH3:22])[CH:20]=[O:21]>>[CH3:18][N:19]1[CH2:22][C:14](=[O:16])[NH:12][C:11]([CH3:10])([CH3:2])[C:20]1=[O:21]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 8082PiperidineHCID 23090132Ethyl N-acetyl-N-methylglycinate

Product 1

HCID 230901071,3,3-Trimethylpiperazine-2,5-dioneYield 59%

Procedure

Piperidine (867 mL) was added to N-[(α,α-dimethyl-(9H-fluoren-9-ylmethoxy)carbamino] acetylsarcosine ethyl ester (743 mg) in N,N-dimethylformamide (20 mL), followed by stirring at room temperature for 1 hour. N,N-Dimethylformamide (60 mL) was added thereto. The resultant mixture was stirred at 80° C. for 14 hours, and cooled in air. The reaction solvent was evaporated under reduced pressure, and the residue was dissolved in ethyl acetate, and then to the resultant solution, hexane was added. The precipitated crystals were recovered by filtration, to thereby give the title compound (162 mg, 59%).

Workup

  1. temperaturecooled in air
  2. customThe reaction solvent was evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. additionto the resultant solution, hexane was added
  5. filtrationThe precipitated crystals were recovered by filtration

Sources & evidence

ORD record
ord-34b15116a7234665bd6ee65e4339cd7a
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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