3,4-Dihydropyrazino[1,2-a]benzimidazol-1(2H)-one → HCID 58044127, compound

HRID 1918894Notes

Reaction equation

HRID 1918894 reaction equation
[C:1]1(=[O:14])[C:6]2=[N:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:5]2[CH2:4][CH2:3][NH:2]1>[Pd].C(O)(=O)C>[C:1]1(=[O:14])[C:6]2=[N:7][C:8]3[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=3[N:5]2[CH2:4][CH2:3][NH:2]1

Participants

4

Reactant 1

HCID 249743893,4-Dihydropyrazino[1,2-a]benzimidazol-1(2H)-one

Product 1

HCID 58044127HCID 58044127, compoundYield 71.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
95 °C

Procedure

A 250-mL stainless steel pressure reactor was charged with 10% palladium on carbon (50% wet, 150 mg dry weight) and a solution of 152b (670 mg, 3.58 mmol) in acetic acid (25 mL). The reactor was evacuated, charged with hydrogen gas to a pressure of 350 psi and stirred at 95° C. for 16 h. After this time, the hydrogen was evacuated, and nitrogen was charged into the reactor. Celite 521 (1.00 g) was added, and the mixture was filtered through a pad of Celite 521. The filter cake was washed with ethanol (2×25 mL), and the combined filtrates were concentrated to dryness under reduced pressure. To the resulting residue was added water (10 mL), and followed by potassium carbonate to adjust pH to 9. The mixture was extracted with methylene chloride (4×20 mL), and the organic extracts were combined, dried over sodium sulfate, filtered and concentrated under reduced pressure to afford a 71% yield 152c (487 mg) as a white solid: mp>250° C.; 1H NMR (500 MHz, DMSO-d6) d 7.86 (s, 1H), 3.98 (t, 2H, J=6.5 Hz), 3.51 (m, 2H), 2.50 (m, 4H), 1.75 (m, 4H); MS (APCI+) m/z 192.6 (M+H).

Workup

  1. customThe reactor was evacuated
  2. additioncharged with hydrogen gas to a pressure of 350 psi
  3. customAfter this time, the hydrogen was evacuated
  4. additionnitrogen was charged into the reactor
  5. additionCelite 521 (1.00 g) was added
  6. filtrationthe mixture was filtered through a pad of Celite 521
  7. washThe filter cake was washed with ethanol (2×25 mL)
  8. concentrationthe combined filtrates were concentrated to dryness under reduced pressure
  9. additionTo the resulting residue was added water (10 mL)
  10. extractionThe mixture was extracted with methylene chloride (4×20 mL)
  11. dry with materialdried over sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-aa9b4d52e0114c988c630500699a63f4
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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