HCID 12901715, compound → HCID 54476306, compound

HRID 1680500Notes

Reaction equation

HRID 1680500 reaction equation
[C:1]1(=[O:15])[CH:6]2[C:7]3[C:12]([C:13](=[O:14])[N:5]2[CH2:4][CH2:3][NH:2]1)=[CH:11][CH:10]=[CH:9][CH:8]=3>[Pd].C1(C)C=CC=CC=1>[C:7]1([CH2:6][C:6]23[C:1](=[O:15])[NH:2][CH2:3][CH2:4][N:5]2[C:13](=[O:14])[C:12]2[C:7]3=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 1

HCID 12901715HCID 12901715, compound

Product 1

HCID 54476306HCID 54476306, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

3,4-Dihydropyrazino[2,1-a]isoindole-1,6(2H, 10bH)-dione (described in Example 6, 10 g, 0.049 mol) is added portionwise to a stirring mixture of 10% palladium on carbon (10 g) in 375 ml of dry toluene. The mixture is refluxed for 20 hr and filtered through Celite (diatomaceous earth). The filtrate is evaporated. The residue is chromatographed on silica gel using acetone-benzene (1:1) and the eluates are evaporated. The residue (5.0 g) is crystallized from acetone-petroleum ether to obtain 10b-phenylmethyl-3,4-dihydropyrazino[2,1-a]isoindole-1,6(2H, 10bH)-dione, mp 202°-204° C., Anal. Calc'd. for C18H16N2O2 : C, 73.95% H, 5.52% N, 9.59% and Found: C, 74.18% H, 5.72% N, 9.57%.

Workup

  1. temperatureThe mixture is refluxed for 20 hr
  2. filtrationfiltered through Celite (diatomaceous earth)
  3. customThe filtrate is evaporated
  4. customThe residue is chromatographed on silica gel
  5. customthe eluates are evaporated
  6. customThe residue (5.0 g) is crystallized from acetone-petroleum ether

Sources & evidence

ORD record
ord-ae596a841ddb421eb93afc5f2970d1d8
Source dataset
uspto-grants-1981_06
Patent number
US04273773

Reaction notes

Loading…