Sodium Hydroxide → HCID 66582841, compound

HRID 1972673Notes

Reaction equation

HRID 1972673 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][CH:10]2[NH:15][C:14](=O)[CH2:13][NH:12][C:11]2=O)[CH:6]=[CH:5][N:4]=1.[OH-].[Na+]>C1COCC1.CO>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][CH:10]2[CH2:11][NH:12][CH2:13][CH2:14][NH:15]2)[CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 665829993-((2-Methoxy-4-pyridinyl)methyl)-2,5-piperazinedione

Product 1

HCID 66582841HCID 66582841, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a 100-mL round-bottomed flask was added 3-((2-methoxy-4-pyridinyl)methyl)-2,5-piperazinedione (398 mg, 1.69 mmol) and borane methyl sulfide complex (0.64 mL, 6.77 mmol, Aldrich, St. Louis, Mo.) in THF (10 mL). The reaction mixture was stirred at 70° C. for 2 h and allowed to cool to room temperature. The reaction mixture was diluted with MeOH (1 mL), followed by 1N NaOH (12 mL), and extracted with DCM (2×50 mL). The organic extract was washed with saturated NaCl (10 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the 2-((2-methoxy-4-pyridinyl)methyl)piperazine as a colorless viscous oil, which was used without further purification.

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with DCM (2×50 mL)
  3. extractionThe organic extract
  4. washwas washed with saturated NaCl (10 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationThe solution was filtered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0429fd7187ad4ee4842c629b27c34005
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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