Water → Ammonia

HRID 582226Notes

Reaction equation

HRID 582226 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]([OH:9])=[O:8].O.[C:11](=[O:14])([OH:13])[O-].[Na+].[CH2:16]([O:23][C:24](Cl)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CC(C)=O.[Pd]>[CH2:16]([O:13][C:11]([N:1]1[CH2:6][CH2:5][N:4]([C:24]([O:23][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:25])[CH2:3][CH:2]1[C:7]([OH:9])=[O:8])=[O:14])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[NH3:1]

Participants

8

Reactant 4

HCID 962WaterHCID 10472-Pyrazinecarboxylic acidHCID 10387Benzyl chloroformateHCID 516892Sodium Bicarbonate2×

Product 2

HCID 222AmmoniaHCID 226328591,4-Bis(benzyloxycarbonyl)piperazine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

2-Pyrazinecarboxylic acid (2.15 g, 17.32 mmol) is placed in a hydrogenation bottle containing water (100 mL), sodium bicarbonate (1.45 g, 17.32 mmol) and palladium black (500 mg). The bottle is placed under hydrogen (40 p.s.i.) for 60 hours, filtered through celite and lyophilized. The residue is dissolved in water (25 mL), cooled to 0° C., and treated with sodium bicarbonate (3.78 g, 45.00 mmol) and benzyloxycarbonylchloride (6.25 mL, 41.60 mmol) in acetone (25 mL). After stirring 20 hours at ambient temperature, the acetone is removed in vacuo and the mixture is partitioned between methylene chloride (200 mL) and water (50 mL). The pH of the aqueous phase is adjusted to 2 with 1N HCl. The organic phase is washed with saline, dried over MgSO4, and concentrated in vacuo to give the title compound, MS (Cl, NH3) m/z 416 [M+NH4 ]+.

Workup

  1. filtrationfiltered through celite
  2. dissolutionThe residue is dissolved in water (25 mL)
  3. customthe acetone is removed in vacuo
  4. customthe mixture is partitioned between methylene chloride (200 mL) and water (50 mL)
  5. washThe organic phase is washed with saline
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a607cd96ea14440bb874a8fdeae996b6
Source dataset
uspto-grants-1999_07
Patent number
US05922707

Reaction notes

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