Diethyl Oxalate → HCID 70423865, compound

HRID 462725Notes

Reaction equation

HRID 462725 reaction equation
Cl.Cl.[CH2:3]([NH:5][CH2:6][C@H:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C@@H:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:9][NH:8]1)[CH3:4].C(N(CC)CC)C.[C:30](OCC)(=[O:36])[C:31](OCC)=[O:32]>C(Cl)(Cl)Cl>[CH2:3]([N:5]1[C:31](=[O:32])[C:30](=[O:36])[N:8]2[CH2:9][C@@H:10]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:11]3[C:16]([C@@H:7]2[CH2:6]1)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH3:4]

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 8471TriethylamineHCID 70423291HCID 70423291, compound

Product 1

HCID 70423865HCID 70423865, compoundYield 60.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of cis-1,2,3,4-tetrahydro-1-(ethylamino)methyl-4-phenyl-isoquinoline dihydrochloride (19.5 g, 0.057 m) in chloroform (250 ml) maintained under nitrogen at ambient temperature was added triethylamine (26.0 g, 0.25 m) and then in one portion diethyl oxalate (36.4 g, 0.23 m) and the mixture heated to reflux for 5 hours. The mixture was cooled and washed with 10% HCl (3×150 ml) and water (200 ml) and dried over MgSO4. The solvent was evaporated to a yellow oil, which was dissolved in 200 ml ethanol, decolorized with Norite. Upon cooling and standing, a white solid crystallized which was collected by filtration and dried to give 11.2 g of cis-1,3,4,6,7,11b-hexahydro-2-ethyl-7-phenyl-2H-pyrazino[2,1-a]isoquinoline-3,4-dione.

Workup

  1. temperatureto reflux for 5 hours
  2. temperatureThe mixture was cooled
  3. washwashed with 10% HCl (3×150 ml) and water (200 ml)
  4. dry with materialdried over MgSO4
  5. customThe solvent was evaporated to a yellow oil, which
  6. dissolutionwas dissolved in 200 ml ethanol
  7. temperatureUpon cooling
  8. customa white solid crystallized which
  9. filtrationwas collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-ec90f983e2244eed95608c180ac16a15
Source dataset
uspto-grants-1985_05
Patent number
US04517187

Reaction notes

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