Sodium hydride → HCID 23121865, compound

HRID 1713522Notes

Reaction equation

HRID 1713522 reaction equation
C1(C[O:8][C:9]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])[CH2:13][CH:12]2[C:27](O)([CH3:29])[CH3:28])=[O:10])C=CC=CC=1.[H-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[C:21]1([CH2:20][O:19][C:17]([N:14]2[CH2:15][CH2:16][N:11]3[C:9](=[O:8])[O:10][C:27]([CH3:29])([CH3:28])[CH:12]3[CH2:13]2)=[O:18])[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 69645610HCID 69645610, compound

Product 1

HCID 23121865HCID 23121865, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Bis(phenylmethyl)2-(1-hydroxy-1-methylethyl)-1,4-piperazinedicarboxylate (1.7 g, 4.2 mmol) was dissolved in N,N-dimethylformamide (20 mL). 60% Sodium hydride (0.25 g, 6.3 mmol) was added thereto, and the mixture was stirred at room temperature for 2 hours. The reaction solution was diluted with ethyl acetate (200 ml), and then washed with an aqueous sodium hydrogen carbonate solution. The extract was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=3:1 to 1:1) and recrystallized from ethyl acetate-hexane to obtain the title compound (0.97 g, yield 76%).

Workup

  1. washwashed with an aqueous sodium hydrogen carbonate solution
  2. washThe extract was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified with silica gel column chromatography (hexane:ethyl acetate=3:1 to 1:1)
  6. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-448ef9b3e2b845998c4857ed868276cc
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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